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[ CAS No. 29310-88-1 ]

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Chemical Structure| 29310-88-1
Chemical Structure| 29310-88-1
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CAS No. :29310-88-1 MDL No. :MFCD00488331
Formula : C11H7BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :267.08 g/mol Pubchem ID :-
Synonyms :

Safety of [ 29310-88-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331-H341 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 29310-88-1 ]

  • Downstream synthetic route of [ 29310-88-1 ]

[ 29310-88-1 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 3949-36-8 ]
  • [ 29310-88-1 ]
YieldReaction ConditionsOperation in experiment
98% With bromine In chloroform for 0.25h; Reflux;
96% With tetra-N-butylammonium tribromide at 20℃; for 1.5h; Green chemistry;
93% With tetra-N-butylammonium tribromide at 20℃; General procedure for the preparation of 2 from 1. General procedure: A mixture of 1 (20 mmol), TBATB (20 mmol), PEG-600 (30 mL) was stirred at RT for 1 - 1 h. After completion of the reaction, the mixture was poured into ice-cold water (60 mL). The separated solid was filtered, washed with water (2×30 mL) and air-dried at RT. The crude product was recrystallized from suitable solvent to obtain pure 2.
90% With bromine In chloroform for 1h; Heating;
90% With copper (II) bromide In chloroform; ethyl acetate for 12.5h; Reflux;
90% With bromine In ethanol; chloroform at 20℃; Heating;
88% With bromine In glacial acetic acid at 70 - 80℃; for 1h;
88% With bromine In chloroform
85% With bromine In chloroform at 50℃; for 0.25h; 4.2.2. 3-(Bromoacetyl)coumarin derivatives (c1-3) General procedure: To a solution of 1 mol b1-3 in 20 mL chloroform was added1 mol of bromine in 5 mL chloroform, with intermittent shakingand warming to decompose an addition product. The mixturewas heated at 50 C for 15 min. on a water-bath to expel most ofthe hydrogen bromide, then cooled and filtered. The solid waswashed with ether and recrystallized with acetic acid. c1-3 wereobtained in 85%, 75% and 80% yields, respectively. Spectral dataof these compounds were matched with the literature [43].
85.7% With bromine In chloroform Reflux;
85% With bromine In chloroform at 50℃; for 0.25h;
81% With bromine; glacial acetic acid at 100℃; for 2h;
80% With bromine; glacial acetic acid for 3h; Ambient temperature;
80.6% With bromine In chloroform at 60℃; for 0.75h;
80% With bromine; glacial acetic acid In chloroform at 20 - 60℃; for 3h; 3.1.3. General Synthesis of 3-bromoacetylcoumarins 3a-c General procedure: 6-Substituted-3-acetylcoumarins 2a-c (15.9 mmol) were dissolved in chloroform (40 mL) andglacial acetic acid (10 mL), then Br2 (15.9 mmol) was carefully added dropwise while stirring thesolution at room temperature. Once the addition of Br2 was finished, the mixture was heated between40-60 °C thus facilitating the emission of hydrobromic acid fumes. After 3 h of reaction, precipitation of3-bromoacetylcoumarin was observed. The solution was allowed to cool to room temperature, filteredand the precipitate washed with three 10 mL portions of cold ethanol. All brominated derivatives wererecrystallized from an 80:20 ethanol/chloroform mixture and characterized by their melting points,1H-NMR, 13C-NMR, and FTIR [56,57].
75% With bromine In 1,4-dioxane; diethyl ether at 30℃; for 1h;
75% With bromine In 1,4-dioxane; diethyl ether for 1h; Ambient temperature;
75% With bromine In glacial acetic acid
75% With bromine In chloroform for 0.25h; Heating;
75% With bromine In chloroform at 0 - 5℃; 4.2. Synthesis of 3-acetylcoumarin (3) and 3-bromoacetylcoumarin (4) 3-Acetylcoumarin (3) (28.2 g, 0.15 mol) was dissolved in alcohol free chloroform (150 mL) and a solution of bromine (7.69 mL, 0.15 mol) in chloroform (20 mL) was added dropwise from a dropping funnel with constant stirring at 0-5 °C. After 4-5 h, a dark yellow solid separated. The reaction mixture was heated for 15 min and CHCl3 was removed using a rotary evaporator. Purification by recrystallization (glacial acetic acid) gave 3-bromoacetylcoumarin (4) (29.8 g, 75%) as light yellow or off white needles, mp 162-165 °C (Lit. mp refPreviewPlaceHolder[22] 160-163 °C) as shown in refPreviewPlaceHolderScheme 1.
75% With NBS; toluene-4-sulfonic acid In acetonitrile at 50℃; for 5h; 2 5.1.2. 3-(2-Bromoacetyl)-2H-chromen-2-one (3) To a solution of 2 (188 mg, 1 mmol) in CH3CN (10 mL) wasadded NBS (182 mg, 1.02 mmol) and p-toluenesulfonic acid(190 mg, 1 mmol). The mixture was stirred at 50 C for 5 h andmonitored by TLC. After completion of reaction, the solvent wasremoved under reduced pressure and the residue was poured into10% NaHCO3 solution (50 mL). The aqueous layer was extractedwith ethyl acetate, washed with brine, dried (Na2SO4), and thenconcentrated in vacuo. The residue was purified by silica gel columnchromatography to provide 3 as a white solid in 75% yield.1H NMR (CDCl3, 400 MHz) d: 4.76 (s, 2H, COCH2Br), 7.37-7.42(m, 2H, ArH), 7.69-7.73 (m, 2H, ArH), 8.65 (s, 1H, CH).
75% With bromine In chloroform at 0 - 5℃; for 0.25h; Synthesis of 3-bromoacetyl coumarin (IV) 3-Acetyl coumarin (III) so obtained was brominated bydissolving 3-acetylcoumarin (0.15 M) in alcohol free chloroform(150 mL) and dropwise adding a solution of bromine(0.15 M) in chloroform (20 mL) with constant stirring at 0-5°C. After 4-5 hours, yellow solid was separated. The reactionmixture was heated for 15 minutes [37].Yield 75%; Lightyellow solid; Mp 162-167 °C (glacial acetic acid); 1H NMR(CDCl3), 4.42 (s, 2H, CH2), 8.41 (s, 1H, coumarin), 7.41-7.81 (m, 4H, aromatic); MS for C11H7BrO3: m/z 266.1; ElementalAnalysis for C11H7BrO3: C, 49.47; H, 2.64; O, 17.97(calcd), C, 49.45; H, 2.62; O, 17.95 (found).
75% With NBS; toluene-4-sulfonic acid In acetonitrile at 60℃; for 12h; 1.2 2) 3-acetyl-2H-benzopyran-2-one (1.88 g, 10 mmol), N-bromosuccinimide (2.67 g, 15 mmol),p-Toluenesulfonic acid (0.95 g, 5 mmol) was placed in a round bottom flask, 100 ml of acetonitrile was added, and the reaction was carried out at 60 ° C for 12 hours.Stop the reaction, add saturated sodium thiosulfate solution, extract with ethyl acetate, combine the organic phase, spin dry,The solid powder was separated and purified by gel column chromatography in a yield of 75%.
70% With copper (II) bromide In ethanol at 100℃; for 0.0333333h; Microwave irradiation;
69% With bromine In chloroform Reflux;
69% With bromine In chloroform at 62 - 64℃; 2 resultant 3-acetyl-2H-chromene-2-one (0.01 mol) was dissolved in dry chloroform and a solution of Br2 (0.01 mol) in chloroform was added dropwise with continuous stirring and mixture was heated at refluxed (62-64 °C) for 6-7 h. The progress of reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, judged by TLC, the reaction mixture was concentrated under reduced pressure, cooled and washed with diethyl ether and recrystallized (70% chloroform/ethanol) to afford 3-(2-bromoacetyl)-2H-chromen-2-one (4) [34]. Yield: 69%; m.p.:151-153 C; Rf: 0.26 (20% EtOAc/hexane); IR (neat, cm1): 2925(CH2), 1716 (CO), 1031 (CAO), 565 (CABr); 1H NMR (300 MHz,DMSO-d6): d 4.90 (s, 2H, CH2), 8.84 (s, 1H, CAH, H-4), 7.24 (d, 1H,J = 7.8 Hz, ArH), 7.13-7.10 (m, 1H, ArH), 6.98-6.95 (m, 1H, ArH),6.88 (d, 1H, J = 7.5 Hz, ArH); 13C NMR (75 MHz, DMSO-d6): d197.4, 154.7, 146.8, 133.5, 130.0, 129.3, 119.8, 119.1, 118.4,116.5, 55.4. Anal. Calcd. for C11H7BrO3: C, 49.49; H, 2.66; found:C, 49.38; H, 2.79.
63% With bromine In chloroform at 0 - 5℃; for 6h;
62% With bromine In chloroform for 0.25h; Heating;
60% With bromine; glacial acetic acid for 1h; Reflux;
48.2% With bromine In chloroform at 0 - 5℃; for 4h; 2.2.1. Synthesis of BAC BAC was synthesized by the reportedmethod [44-48]. 3-Acetyl coumarin(ACO) (10 mmol) was dissolved in alcohol-free chloroform(30mL) and a solution of bromine (10mmol) in alcohol free chloroform(5 mL)was added dropwise froman equilibrating funnel,with constantstirring at 0-5 °C. After 4 h, the reaction mixture was heated for 15minand CHCl3 was removed by rotary evaporator. The solid obtained waswashed by ether. Purification by recrystallization from glacial aceticacid gave 3-bromoacetylcoumarin aswhite shiny needles in good yields(Yield, 48.2%). FT-IR (KBr, cm-1): 3026 (Ar-H), 2961 (C-H), 1725(C=O), 1616, 1564, 1449 (Ar, C=C), 1185, 1146 (C-O-C), C-Br(541). Exp. 320.8684. Elemental analysis (calcd. %) forC11H7BrO3·0.5H2O: C, 47.85; H, 2.92; Found: C, 47.84; H, 3.38. Exactmass for BAC: 265.9579, HR-MS (positive mode) [BAC+Na+]+ (m/z,cal. 288.9476; Exp. 288.8521), [BAC + H+ + 3H2O]+ (m/z, Cal.320.9974. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.71 (ddd, J =7.4,4.2, 1.3 Hz, 2H), 7.56 (s, 1H), 7.51-7.35 (m, 2H), 4.76 (s, 1H). 13C NMR(101 MHz, CDCl3) δ 188.89 (s), 159.10 (d, J = 14.3 Hz), 155.34 (s),149.52 (s), 135.17 (s), 130.47 (s), 125.34 (s), 118.14 (s), 117.01 (s),and 35.71 (s).
44% With NBS; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 2h; 2 Preparation of 3-(2-bromoacetyl)-2H-benzopyran-2-one A mixture of 3-acetyl-2H-benzopyran-2-one (188 mg, 1 mmol), p-toluenesulfonic acid (380 mg, 2 mmol), N-bromosuccinimide (354 mg, Mmol was placed in a round bottom flask, 10 mL of DMF was added and reacted at 100 ° C for 2 hours. TLC showed the reaction was complete, the reaction was stopped, saturated sodium thiosulfate solution was added and extracted with ethyl acetate. The organic phases were combined and purified by silica gel column chromatography , The white solid powder 127 mg, the yield of 44%.
44% With NBS; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 2h; 2 Preparation of 3-(2-bromoacetyl)-2H-benzopyran-2-one A mixture of 3-acetyl-2H-benzopyran-2-one (188 mg, 1 mmol), p-toluenesulfonic acid (380 mg, 2 mmol), N-bromosuccinimide (354 mg, Mmol was placed in a round bottom flask, 10 mL of DMF was added and reacted at 100 ° C for 2 hours. TLC showed the reaction was complete, the reaction was stopped, saturated sodium thiosulfate solution was added and extracted with ethyl acetate. The organic phases were combined and purified by silica gel column chromatography , The white solid powder 127 mg, the yield of 44%.
With chloroform; bromine
With bromine In chloroform
With bromine In chloroform
With bromine In Carbon tetrachloride for 0.0833333h; Heating;
With bromine In chloroform Heating;
In chloroform at 20℃;
With bromine In chloroform
With bromine In chloroform at 20℃; for 1h;
With bromine; glacial acetic acid for 2h; Reflux;
With 2,2'-azobis(isobutyronitrile); bromine In glacial acetic acid at 60 - 70℃; for 0.25h; 2. Experimental Salicylaldehyde, ethylacetoacetate, piperidine, glacial acetic acid, ethanol, bromine, and azoisobuteronitrile (AIBN) fromSigma.Aldrich Chemical Company with a stated purity greater than 99% were used without further purification to synthesize the title compound. 3-Bromoacetylcoumarin was synthesized in a two stage process, viz., Knoevenagel condensation and bromination. In the first stage, a mixture of salicylaldehyde (0.01 mmol), ethylacetoacetate (0.01 mmol), piperidine (4 drops), glacial acetic acid (2 drops) and ethanol (20 ml) was refluxed for 5 h and the reaction mixture was poured into cold water, filtered, washed and dried to yield 3-acetylcoumarin. The bromination of 3-acetylcoumarin was carried out using bromine in glacial acetic acid (0.01 mmol) and AIBN as catalyst at about 60-70 °C for 15 min. The crystals of 3-bromoacetylcoumarin formed were collected, washed with minimum quantity of glacial acetic acid, dried and purified by repeated recrystallization from glacial acetic acid to obtain larger size crystalsof dimension 28 mm x 7 mm x 3 mm. Purity of the compound was checked by thin layer chromatography. The infrared spectrum of the sample was recorded between 4000 cm1 and 400 cm1 on a JASCO 400 FT-IR spectrometer that was calibrated using polystyrene bands. The sample was prepared as a KBr disc. The FT-Raman spectrum of the sample was recorded the 3500-50 cm1 region on a Bruker RFS 100/S FT-Raman spectrometer using the 1064 nm excitation from a Nd:YAG laser and a liquid nitrogen cooled Ge detector.
With bromine; glacial acetic acid In chloroform at 20℃;
With bromine In chloroform
With bromine In chloroform for 4h;
With bromine In chloroform
With bromine In chloroform
With bromine In chloroform at 20 - 60℃; for 1h;
With bromine In chloroform at 60℃;
With bromine In chloroform
With NBS; toluene-4-sulfonic acid In chloroform; acetonitrile for 4h; Reflux; General procedure (exemplified for 1a) A solution of 3-acetylcoumarin derivatives (10 mmol, 1,880 mg), NBS (11 mmol, 1,958 mg), and p-toluenesulfonic acid (1 mmol, 172 mg) in chloroform-acetonitrile (25:5) were magnetically stirred at reflux. After completion of the reaction [about 4 h; TLC (AcOEt/hexane 1:3)], the mixture was cooled and the precipitate was filtered and washed with EtOH (10 ml) to afford the pure product 3-(2-bromoacetyl)coumarin derivatives (Scheme 2).
With bromine In ethanol at 20℃;
With bromine In chloroform at 50℃; for 0.25h;
With bromine In chloroform at 0 - 5℃; General procedure for the synthesis of 3-acetylcoumarins (3a-g) and 3-bromoacetyl coumarins (6a, b) General procedure: Mixture of various salicylaldehyde (1a-g) (0.20 mol) and ethyl acetoacetate 2 (0.25 mol) was cooled and maintained at 0-5 °C. Few drops of piperidine was added drop wise with continuous stirring. The reaction mixture was left overnight, resulting in the formation of yellow colored solid which was washed by ether and recrystallized by ethanol/CHCl3 1:3 mixture, to afford pure 3-acetylcoumarins (3a-g) as fine yellow needles in good yields. Various 3-acetylcoumarins (3a-g) (0.15 mol) were dissolved in alcohol-free chloroform (150 mL) and a solution of bromine (0.15 mol)in alcohol free chloroform (20.0 mL) was added drop-wise from an equilibrating funnel, with constant stirring at 0-5 °C. After 4-5 h, a dark yellow solid separated. The reaction mixture was heated for 15 min on water bath and CHCl3 was removed by rotary evaporator. The solid obtained was washed by ether. Purification by recrystallization from glacial acetic acid gave 3-bromoacetylcoumarins (6a, b) as white shiny needles in good yields.
With bromine In chloroform at 20℃; for 1.5h; Reflux; General procedure for the synthesis of 3-(2-bromoacetyl)-6-H/halo-2H-chromen-2-one (4a-4e) General procedure: To a mixture of appropriate compound (3a-3e) (0.25 moles)in 200 mL of alcohol free chloroform, bromine (0.30 moles)in 25 mL of chloroform was added drop wise with stirring.The reaction mixture was first stirred for 1 h at room temperatureand then it was refluxed for about 30 min. Thereaction mixture was cooled, solid mass was separated,washed with diethyl ether and recrystallized from aceticacid.
With NBS; citric acid In ethanol; lithium hydroxide monohydrate for 0.333333h; Reflux;
With bromine In chloroform at 0 - 5℃;
With bromine In chloroform at 20℃;
With bromine; glacial acetic acid for 2h; Reflux; Synthesis of 3-(bromoacetyl)-2H-chromen-2-one 2a Compound 8a (3.764 g, 20 mmol) is dissolved in acetic acid(20 mL) and a solution of bromine (1.03 mL, 20 mmol) in acetic acid (10 mL) was added drop wise with stirring. Themixture is heated at reflux for 2 h, then it is cooled and the crude solid is collected by filtration. The solid was washedby water to give 3-(bromoacetyl)coumarin 2a (3.205 g, 60 %) as an intense yellow solid; m.p. 167-168 °(168).
With bromine In glacial acetic acid
With bromine; glacial acetic acid
With bromine In chloroform 8 3-(Bromoacetyl)chromone. EXAMPLE 8 SPC13 3-(Bromoacetyl)chromone. A solution of 1.6g (0.01 mole) of bromine in 10ml of chloroform was added over a period of 5 minutes to a stirred solution of 1.88g (0.01 mole) of 3-acetylchromone. [RE: F. Eiden and H. Havenland, Arch. Pharm., 300, 806 (1967)]. After one-half hour the solvent was removed to give 1.9g (70%) of crude product; m.p. 140°-145°. Recrystallization from ethyl acetate gave pure product; m.p. 151°-153°. Anal. Calcd. for C11 H7 BrO3: C, 49.47; H, 2.64; Br, 29.92. Found: C, 49.57; H, 2.88; Br, 30.20.
With tetra-N-butylammonium tribromide In glacial acetic acid for 2h;
With tetra-N-butylammonium tribromide In glacial acetic acid at 20℃; for 2h;
With bromine; glacial acetic acid Synthesis of 3-bromoacetylcoumarin (3) 3-Acetylcoumarinwas synthesized by Knoevenagel condensation. A mixture of salicylaldehyde (0.01 mmol), ethylacetoacetate (0.01 mmol), piperidine (4 drops), glacial acetic acid (2 drops) and ethanol (20 mL) was refluxed for 5 h and the reaction mixture was poured into cold-water, filtered, washed and dried to yield 3-acetylcoumarin (3). It was then brominated using bromine in acetic acid (0.01 mmol). The crystals of 3-bromoacetyl coumarin(4) formed were collected, washed with minimum quantity ofglacial acetic acid, dried and recrystallized [19].
With bromination agent In chloroform
With bromine In chloroform
With copper (II) bromide In chloroform; ethyl acetate Reflux;
With bromine; glacial acetic acid at 20℃; for 5h;
With copper (II) bromide In chloroform; ethyl acetate
With bromine In chloroform for 0.583333h;
With copper (II) bromide In ethanol
With trifluoroacetic acid; copper (II) bromide at 140℃; for 0.25h; Microwave irradiation;
With bromine In chloroform for 0.583333h; Synthesis of 3-(bromoacetyl)-coumarin (2) and 2-bromo-1-phenylethan-1-one (4) General procedure: 3-(Bromoacetyl)-coumarin (II) and 2-bromo-1-phenylethan-1-one were prepared by the methods reported in the literature[53]. 3-Acetylcoumarin 1 (10mmol) and acetophenone(10mmol) were dissolved in alcohol-free chloroform (20mL)and a solution of bromine (10 mmol) in chloroform (5 mL)was added dropwise from a dropping funnel. The mixture wasstirred at room temperature for 15min, then the mixture washeated for 20min on a water-bath to expel most of thehydrogen bromide. The solid obtained was washed by etherand purification by recrystallization from glacial acetic acid gave 3-(bromoacetyl)-coumarin or 2-bromo-1-phenylethan-1-one as white shiny needles in good yields.
With bromine; glacial acetic acid at 20℃; for 6h;

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[32]Current Patent Assignee: JISHOU UNIVERISITY - CN104829608, 2017, B Location in patent: Paragraph 0028-0030
[33]Koelsch [Journal of the American Chemical Society, 1950, vol. 72, p. 2993]
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[44]Location in patent: scheme or table Hamama, Wafaa S.; Berghot, Moged A.; Baz, Eman A.; Gouda, Moustafa A. [Archiv der Pharmazie, 2011, vol. 344, # 11, p. 710 - 718]
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[53]Kurt, Belma Z.; Sonmez, Fatih; Gokce, Basak; Ergun, Adem; Gencer, Nahit; Demir, Taki; Arslan, Oktay; Kucukislamoglu, Mustafa [Russian Journal of Bioorganic Chemistry, 2016, vol. 42, # 5, p. 506 - 511][Bioorg. Khim.]
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[69]Abdelrahman, Mohamed A.; Ibrahim, Hany S.; Nocentini, Alessio; Eldehna, Wagdy M.; Bonardi, Alessandro; Abdel-Aziz, Hatem A.; Gratteri, Paola; Abou-Seri, Sahar M.; Supuran, Claudiu T. [European Journal of Medicinal Chemistry, 2021, vol. 209]
[70]Wang, You-Xian; Liu, Shu-Hao; Shao, Zhong-Bai; Cao, Lian-Gong; Jiang, Kai-Jun; Lu, Xing; Wang, Lei; Liu, Wei-Wei; Shi, Da-Hua; Cao, Zhi-Ling [Journal of Chemical Research, 2021, vol. 45, # 5-6, p. 359 - 364]
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[72]Özkütük, Müjgan; Aydıner, Burcu; Erer, Hakan; Kandemir, Ebubekir; Seferoğlu, Nurgül; Seferoğlu, Zeynel [Journal of Molecular Structure, 2022, vol. 1249]
[73]Alvarado-Méndez, Edgar; Flores-Alamo, Marcos; García-Revilla, Marco A.; Peña-Cabrera, Eduardo; Trejo-Durán, Mónica; Vázquez, Juan Luis; Vázquez, Miguel A.; Velazco-Cabral, Iván [Physical Chemistry Chemical Physics, 2021, vol. 23, # 39, p. 22466 - 22475]
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[75]Abdel-Aziz, Hatem A.; Abdelrahman, Mohamed A.; Afarinkia, Kamyar; Al-Warhi, Tarfah; Aljaeed, Nada; Alotaibi, Ohoud J.; Elbadawi, Mostafa M.; Eldehna, Wagdy M.; Elimam, Diaaeldin M.; Mahdy, Hazem A.; Nocentini, Alessio; Supuran, Claudiu T.; Taghour, Mohammed S. [Journal of Enzyme Inhibition and Medicinal Chemistry, 2022, vol. 37, # 1, p. 531 - 541]
  • 2
  • [ 29310-88-1 ]
  • [ 17356-08-0 ]
  • [ 61636-28-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium fluoride In methanol; water at 20℃; General procedure for the synthesis of 1,3-thiazoles and selenazoles General procedure: The appropriate phenacylbromide or 3-(2-bromoacetyl)-2H-chromen-2-one (1mmol) and either thiourea, phenylthiourea or selenourea (1mmol) were dissolved in 2mL of methanol, water (2mL) containing 0.02g of NaF added and the mixture stirred at room temperature for the appropriate time. After completion of the reaction, 10mL of water was added and the solid that separated out was filtered off and washed with water, affording analytically pure substituted 1,3-thiazoles or 1,3-selenazole derivatives in excellent yields.
98% In water at 25℃; for 0.0111111h; Sonication; Green chemistry; General procedure for the synthesis of 2,4-disubstituted-1,3-thiazolesand selenazoles (3-16) General procedure: A 100-mL borosil test-tube was charged with phenacyl bromide (1a-h)/3(2-bromoacetyl)coumarin (1i-n) (1 mmol), thiourea (2a)/phenylthiourea (2b)/selenourea(2c) (1 mmol) and water (1 mL). The tube was kept in such a way that thesurface of the reactants is just lower than the water level of the ultrasonic bath inwhich they were sonicated with a frequency of 50 kHz at 25 C for about 10-60 s.The progress of the reaction was monitored by TLC. After completion of thereaction, the solid separated out was filtered and washed with water. Analyticallypure products were obtained without further recrystallization.
96% at 20℃; 4.2 General procedure for the synthesis of 2-(3-pyridyl)/2-amino thiazole derivatives (3/5) General procedure: A mixture of phenacyl bromide (1a) (10.0mmol), pyridine-3-carbothioamide/thiourea (2/4) (10.0mmol) and 5.0wt% of silica-supported HClO4 was taken in a mortar and ground together with a pestle for 5-10min at RT. At this stage, the progress of the reaction was monitored by TLC. After completion of the reaction, the crude mass was washed with water (20mL) twice and extracted with ethyl acetate (10mL) twice. Then the catalyst was separated by filtration under vacuum. The organic layer was washed with water, dried with anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The obtained product (3a/5a) was purified by recrystallization using ethanol. The same procedure was applied for the preparation of all other compounds (3b-k & 5b-k). All the compounds gave satisfactory physical and spectroscopic data following their proposed procedure. Compounds 5a-d and 5f-5k were synthesized and reported in the literature [82,83].
93% In ethanol for 0.25h; Heating;
91% In ethanol 3.1.4. General Synthesis of 6-substituted-3-(2-amino-thiazol-4-yl)-coumarins 4a-c General procedure: To an ethanol solution (150 mL) of 6-substituted-3-bromoacetilcoumarin 3a-c (6.3 mmol) at 50 °C an equimolar amount of thiourea was added with vigorous stirring and maintained at 70 °C. Ten min after the addition of thiourea, the mixture turned to an intense orange-yellow color and furtherprecipitation of a yellow solid was observed. After evaporation of the solvent to 50% of the initialvolume, the mixture was cooled, the solid filtered out and washed with cold ethanol. The yellowsolid was dissolved in 200 mL of a hot solution of 10% ammonium acetate in water, stirred for10 min and then allowed to cool to room temperature. The solids corresponding to 4a-c were filtered.All compounds were recrystallized from ethanol and characterized by their melting points, 1H-NMR,13C-NMR and FTIR.
90% In tetrachloromethane for 0.0833333h; Heating;
90% In ethanol for 1h; Reflux;
89.67% In ethanol for 3h; Reflux;
84% In ethanol for 1h; Heating;
80% In ethanol at 80℃;
69% In ethanol for 12h; Reflux;
68% In ethanol Heating;
With ethanol
In ethanol Reflux;
With triethylamine In ethanol Reflux;
With triethylamine In ethanol; N,N-dimethyl-formamide for 8h; Reflux;
With sodium fluoride at 20℃;
In ethanol for 1h; Reflux; 4.2.3. 3-(2-Amino-1,3-thiazol-4-yl)coumarin derivatives (d1-3) General procedure: Thiourea (5 mmol) was added to the solution of c1-3 (5 mmol)in boiling ethanol (20 mL). The mixture was refluxed for 1 h, thencooled and neutralized with aqueous ammonia. The precipitatewas filtered off, washed with ethanol and used directly without crystallization or other purification. d1-3 were obtained in 80%,78% and 75% yields, respectively. Spectral data of these compoundswere matched with the literature [44].
In ethanol Heating;
In ethanol
In ethanol for 1h; Reflux;
Reflux;
In ethanol Heating;

Reference: [1]Banothu, Janardhan; Vaarla, Krishnaiah; Bavantula, Rajitha; Crooks, Peter A. [Chinese Chemical Letters, 2014, vol. 25, # 1, p. 172 - 175]
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[15]Location in patent: scheme or table Yaragatti, Naazneen B.; Kulkarni, Manohar V.; Ghate, Manjunath D.; Hebbar, Satyanarayan S.; Hegde, Ganesh R. [Journal of Sulfur Chemistry, 2010, vol. 31, # 2, p. 123 - 133]
[16]Location in patent: scheme or table Hamama, Wafaa S.; Berghot, Moged A.; Baz, Eman A.; Gouda, Moustafa A. [Archiv der Pharmazie, 2011, vol. 344, # 11, p. 710 - 718]
[17]Location in patent: scheme or table Gouda, Moustafa A.; Berghot, Moged A.; Baz, Eman A.; Hamama, Wafaa S. [Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1062 - 1070]
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[21]Şahin, Ömer; Özdemir, Ümmühan Özmen; Seferoğlu, Nurgül; Aydıner, Burcu; Sarı, Musa; Tunç, Tuncay; Seferoğlu, Zeynel [Tetrahedron, 2016, vol. 72, # 39, p. 5843 - 5852]
[22]Kurt, Belma Z.; Sonmez, Fatih; Gokce, Basak; Ergun, Adem; Gencer, Nahit; Demir, Taki; Arslan, Oktay; Kucukislamoglu, Mustafa [Russian Journal of Bioorganic Chemistry, 2016, vol. 42, # 5, p. 506 - 511][Bioorg. Khim.]
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[24]Özkütük, Müjgan; Aydıner, Burcu; Erer, Hakan; Kandemir, Ebubekir; Seferoğlu, Nurgül; Seferoğlu, Zeynel [Journal of Molecular Structure, 2022, vol. 1249]
  • 3
  • [ 29310-88-1 ]
  • [ 880-29-5 ]
  • [ 34560-08-2 ]
  • 4
  • [ 29310-88-1 ]
  • [ 103-85-5 ]
  • [ 33856-02-9 ]
YieldReaction ConditionsOperation in experiment
98% With sodium fluoride In methanol; water at 20℃; General procedure for the synthesis of 1,3-thiazoles and selenazoles General procedure: The appropriate phenacylbromide or 3-(2-bromoacetyl)-2H-chromen-2-one (1mmol) and either thiourea, phenylthiourea or selenourea (1mmol) were dissolved in 2mL of methanol, water (2mL) containing 0.02g of NaF added and the mixture stirred at room temperature for the appropriate time. After completion of the reaction, 10mL of water was added and the solid that separated out was filtered off and washed with water, affording analytically pure substituted 1,3-thiazoles or 1,3-selenazole derivatives in excellent yields.
94% In water at 25℃; for 0.0125h; Sonication; Green chemistry; General procedure for the synthesis of 2,4-disubstituted-1,3-thiazolesand selenazoles (3-16) General procedure: A 100-mL borosil test-tube was charged with phenacyl bromide (1a-h)/3(2-bromoacetyl)coumarin (1i-n) (1 mmol), thiourea (2a)/phenylthiourea (2b)/selenourea(2c) (1 mmol) and water (1 mL). The tube was kept in such a way that thesurface of the reactants is just lower than the water level of the ultrasonic bath inwhich they were sonicated with a frequency of 50 kHz at 25 C for about 10-60 s.The progress of the reaction was monitored by TLC. After completion of thereaction, the solid separated out was filtered and washed with water. Analyticallypure products were obtained without further recrystallization.
85% at 20℃; for 0.25h; Neat (no solvent); grinding;
56% In ethanol for 12h; Heating;
In ethanol Heating;
In ethanol Reflux;

  • 5
  • [ 7357-70-2 ]
  • [ 29310-88-1 ]
  • [ 88735-45-9 ]
YieldReaction ConditionsOperation in experiment
88% In ethanol for 2h; Reflux;
88% In ethanol for 2h; Reflux; Procedure for the preparation of 3 from 2 A mixture of 2 (10 mmol) and 2-cyanothioacetamide (10 mmol) was refluxed in ethanol (30 mL) for a period of 2 h. After completion of the reaction as indicated by TLC, the reaction mixture was poured into ice-cold water (100 mL). The separated solid was filtered, washed with water (2×50 mL) thoroughly, air dried at RT. The product was recrystallized from methanol to obtain a pure colorless compound 3. White solid. Yield: 2.35 g (88%); M.p. 177-179°C; IR (KBr): 1730 cm-1 (strong, sharp, -CO of coumarin ring), 2206 cm-1 (strong, sharp, -CN group); 1H NMR (400MHz, DMSO-d6/TMS): δ = 4.66 (s, 2H, -CH2) 7.38-7.98 (multiplet, 4H, Ar-H), 8.43 (s, 1H, Ar-H), 8.78 (s, 1H, Ar-H); 13C NMR (100MHz, DMSO-d6/TMS): 21.50, 115.8, 116.9, 118.9, 119.8, 121.1, 124.7, 129.1, 132.1, 139.5, 147.3, 152.5, 158.6, 158.9; HRMS calculated for C14H9N2O2S [M+H]+: 269.0384, Found: 269.0321.
83% In ethanol for 0.25h; Heating;
68% In ethanol; isopropyl alcohol Heating;
60% In ethanol for 0.5h; Heating;

  • 6
  • [ 29310-88-1 ]
  • [ 58952-14-0 ]
  • [ 88735-50-6 ]
YieldReaction ConditionsOperation in experiment
87% In ethanol for 0.25h; Heating;
  • 7
  • [ 29310-88-1 ]
  • [ 40207-02-1 ]
  • [ 129545-40-0 ]
YieldReaction ConditionsOperation in experiment
78% With pyridine In methanol for 1h; Heating;
  • 8
  • [ 29310-88-1 ]
  • [ 62-55-5 ]
  • [ 106578-02-3 ]
YieldReaction ConditionsOperation in experiment
82% In ethanol; isopropyl alcohol Heating;
79% In methanol at 20℃; for 4.5h; Reflux; 2.1 2.1. Synthesis of 3 (2 Methyl thiazol 4 yl) 2H chromen 2 one (2) 3 (2 Bromoacetyl) 2H chromene 2 one (0.01mol) (1) was dissolvedin 30 mL of methanol followed by the addition of thioacetamide (0.01 mol) in methanol and stirred at room temperature for 30 min .The resulting mixture was refluxed for 4 h and, at completion monitored by TLC, the reaction mixture was poured into ice-cold water.The product (2) was recrystallized by slow evaporation from methanol.Yield: 79%; Yellowish brown crystals; m.p.: 259-261 °C; Rf: 0.36; FTIR(ATR, υ/cm-1): 3077 (Csp2-H), 1693 (C_O), 1605 (C_N), 1538(C_C aromatic); 1H NMR (300MHz, CDCl3): δ 8.73 (s, 1H, H-4 lactone),7.64 (d, J=6.9 Hz, 1H,ArH), 7.54 (dd, J=7.6, 1.2 Hz, 1H, ArH); 8.31(s, 1H, thiazole) 7.28-7.21 (m, 2H, ArH); 2.91 (s, 3H, CH3); 13C NMR(75 MHz, DMSO d6): δ 163.2 (C_N, thiazole), 160.8 (C_O, lactone),152.7, 144.0, 140.3, 139.2, 132.2, 129.4, 129.4, 123.1, 120.6, 117.6,57.2;LC-MS (m/z): 243.0 (M)+; Elemental analysis Found (%): C, 64.18; H,3.73; N, 5.76; S, 13.18; Calc. for C13H9NO3: S: C, 64.21; H, 3.71; N, 5.69;S, 13.20.
With N,N-dimethyl-formamide In ethanol for 4h; Heating; Yield given;
  • 9
  • [ 29310-88-1 ]
  • [ 17356-08-0 ]
  • 3-(2-amino-1,3-thiazol-5-yl)-2H-1-benzopyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In ethanol for 1h; Reflux; Synthesis of 3-(2-amino-1,3-thiazol-4-yl)coumarin(3) and 5-phenylthiazol-2-amine (5) General procedure: 3-(2-Amino-1,3-thiazol-4-yl)coumarin and 5-phenylthiazol-2-amine were prepared by a mixture of Thiourea (5mmol) anda solution of 3-(bromoacetyl)-coumarin (5 mmol) or 2-bromo-1-phenylethan-1-one in boiling ethanol (20mL). The mixturewas refluxed for 1 h, then cooled and neutralized with aqueousammonia (NH4Cl). The solid obtained was filtered offand washed with ethanol without recrystallization or otherpurification. The product was obtained in 90% yield [54].3-(2-Amino-1,3-thiazol-4-yl)coumarin (3)It was obtained as a yellow powder. Yield: 90%; m.p.228-229 °C; 1H-NMR (400MHz, DMSO-d6) δ 8.51 (s, 1H),7.82 (d, J=7.7 Hz, 1H), 7.61 (ddd, J=8.9, 7.3, 1.7 Hz, 1H),7.51 (s, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.37 (td, J=7.5,1.1Hz, 1H), 7.19 (s, 2H); 13C-NMR (101MHz, DMSO-d6) δ167.93, 159.21, 152.66, 138.60, 131.94, 131.47, 129.14,125.14, 120.87, 119.75, 116.71, 116.28, 109.18.
90% In ethanol for 1h; Reflux; Synthesis of 3-(2-amino-1,3-thiazol-4-yl)coumarin(3) and 5-phenylthiazol-2-amine (5) General procedure: 3-(2-Amino-1,3-thiazol-4-yl)coumarin and 5-phenylthiazol-2-amine were prepared by a mixture of Thiourea (5mmol) anda solution of 3-(bromoacetyl)-coumarin (5 mmol) or 2-bromo-1-phenylethan-1-one in boiling ethanol (20mL). The mixturewas refluxed for 1 h, then cooled and neutralized with aqueousammonia (NH4Cl). The solid obtained was filtered offand washed with ethanol without recrystallization or otherpurification. The product was obtained in 90% yield [54].3-(2-Amino-1,3-thiazol-4-yl)coumarin (3)It was obtained as a yellow powder. Yield: 90%; m.p.228-229 °C; 1H-NMR (400MHz, DMSO-d6) δ 8.51 (s, 1H),7.82 (d, J=7.7 Hz, 1H), 7.61 (ddd, J=8.9, 7.3, 1.7 Hz, 1H),7.51 (s, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.37 (td, J=7.5,1.1Hz, 1H), 7.19 (s, 2H); 13C-NMR (101MHz, DMSO-d6) δ167.93, 159.21, 152.66, 138.60, 131.94, 131.47, 129.14,125.14, 120.87, 119.75, 116.71, 116.28, 109.18.
86% In ethanol for 2h; Heating;
70% In ethanol at 20℃;
66% In ethanol for 4h; Heating;

  • 10
  • [ 29310-88-1 ]
  • [ 62-53-3 ]
  • [ 88735-81-3 ]
YieldReaction ConditionsOperation in experiment
91% In ethanol Heating;
72% In ethanol for 0.25h; Heating;
70% With sodium hydrogencarbonate In ethanol for 5h; Reflux; 5. General procedure for the synthesis of 3',6,8-substituted 3-(2-phenylaminoacetyl)-2H-chromen-2-one derivatives 13-20 General procedure: A solution of the opportune amine (aniline, 3-aminobenzoic acid, ethyl 3-aminobenzoate) (0.0021 mol), NaHCO3 (0.176 g, 0.0021 mol) and the appropriately substituted α-bromocetyl-2H-chromen-2-ones 6-12 (0.0021 mol) in 10 mL of ethanol was refluxed for 5 h (TLC analysis). After cooling, the precipitate which formed was collected and derivatives 13-20 resulted sufficiently pure to be used in the next reaction without further purification.
With potassium carbonate at 20℃; Neat (no solvent);

  • 11
  • [ 29310-88-1 ]
  • [ 603-35-0 ]
  • [ 140445-65-4 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane at 20℃; for 1.5h;
100% In dichloromethane at 20℃; for 1.5h; 3-(Triphenylphosphinylacetyl)coumarin bromide (35): Bromide 35 was synthesized from 3-(bromoacetyl)coumarin (2mmol) in 5 mL OfCH2Cl2 and triphenylphosphine (2 mmol). The mixture was stirred 1.5 h at room temperature. The volatiles were removed under reduced pressure. The crude product was tritured with diethyl ether, filtered and washed again with diethyl ether to obtain a yellow crystalline solid (100% yield), mp 127 - 129 0C (dec). 1H NMR (CDCl3) δ 9.24 (s, IH), 7.83 (m, 6H), 7.60 (m, 1 IH), 7.23 (m, 2H), 6.35 (d, 2H,J= 12.2 Hz). 13C NMR δ 189.2, 158.3, 155.4, 151.4, 135.1, 134.3, 133.8, 132.5, 131.5, 130.5, 130.2, 129.1, 125.4, 119.2, 118.0. HRMS (FAB) calcd for C29H22O3P ([M]+): 449.1379, found 449.1313.
97% In benzene for 1h; Heating;
90% In dichloromethane at 20℃; for 1.5h; 2.2.2. Synthesis of TACB Following the reported method to prepare the TACB [45-47], 3-((triphenylphosphinyl)acetyl)coumarin bromide (TACB) was synthesizedfrom 3-(bromoacetyl)coumarin (2 mmol) in 5 mL of CH2Cl2 andtriphenylphosphine (2 mmol). The mixture was stirred for 1.5 h atroom temperature. The volatiles were removed under reducing pressure.The crude product was triturated with diethyl ether, filtered,washed again with diethyl ether and dried in vacuo to obtain a yellowcrystalline solid (90% yield). FT-IR (KBr, cm-1): 3064 (Ar-H), 2807(C-H), 1739 (C=O), 1609, 1558, 1487, 1429 (Ar, C=C), 1183, 1133(C-O-C), C-P (979). Elemental analysis (calcd. %) for C29H22O3PBr([TACB]+Br-}): C, 65.80; H, 4.19; Found: C, 65.80; H, 4.22. Exactmass for TACB: 449.1301, HR-MS (positive mode) [TACB]+ (m/z, cal.449.0301; Exp. 448.9849). 1H NMR (400 MHz, DMSO) δ 9.46 (s, 1H),8.64 (s, 1H), 7.98-7.90 (m, 2H), 7.76-7.63 (m, 6H), 7.54 (td, J = 7.6,3.3 Hz, 3H), 7.41 (d, J = 3.9 Hz, 1H), 7.39 (d, J = 2.5 Hz, 1H), 7.36 (d,J = 3.4 Hz, 1H), 7.33 (s, 1H), 7.31 (d, J = 2.2 Hz, 1H), 7.29 (s, 1H),7.27 (s, 1H), 6.46 (s, 1H), 6.43 (s, 1H). 13C NMR (101 MHz, DMSO) δ190.44 (s), 188.69 (s), 187.75 (s), 159.46 (s), 159.06 (s),155.57-155.17 (m), 154.80 (s), 151.05 (s), 150.32 (s), 150.09 (s),147.80 (s), 136.48 (s), 136.05 (s), 132.10 (s), 131.80 (s), 131.60 (s), 125.91 (t, J = 7.4 Hz), 125.52 (s), 121.81 (d, J = 10.6 Hz),118.76-118.27 (m), 117.18-116.44 (m), and 56.08 (s).

  • 12
  • [ 29310-88-1 ]
  • [ 3696-00-2 ]
  • [ 116317-17-0 ]
YieldReaction ConditionsOperation in experiment
82% With sodium carbonate In ethanol for 6h; Reflux; General procedure for the synthesis of 4-(coumarin-3-yl)-2-((3,5-dimethyl-4-phenyldiazenyl)pyrazol-1-yl)thiazoles (1a-1g) General procedure: An ethanolic solution (20 mL) of 3-bromoacetylcoumarin(7, 0.52 g, 2.00 mmol), sodium carbonate (0.11 g, 1.00 mmol) and 3,5-dimethyl-4-(p-chlorophenyl)diazenylpyrazole-1-thiocarboxamide (5a) (0.59 g, 2.00 mmol) was refluxed on awater bath for 6 h. On completion of the reaction as observed using TLC (20:80, Ethylacetate:Hexane (v/v)), the solvent was evaporated. The solid thus obtained was dissolved in chloroform(25 mL) and washed with water (50 mL). The organic layer was separated and the excesssolvent was distilled off. The solid thus obtained was crystallized with ethanol to afford 1a in82% yield. The protocol was further extended using differently substituted amines and coumarinwhich resulted into the formation of compounds 1b-1g in good to excellent yield.
80% In ethanol; N,N-dimethyl-formamide for 4h; Heating;
  • 13
  • [ 29310-88-1 ]
  • [ 3287-79-4 ]
  • [ 78765-48-7 ]
  • 14
  • [ 29310-88-1 ]
  • [ 25369-78-2 ]
  • [ 78765-46-5 ]
YieldReaction ConditionsOperation in experiment
85% In ethanol for 2h; Heating;
  • 15
  • [ 29310-88-1 ]
  • [ 68029-49-2 ]
  • (E)-3-(furan-2-yl)-2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In N,N-dimethyl-formamide at 20℃; for 24.5h; 2-[4-Aryl(hetaryl, cyclopropyl)thiazol-2-yl]-3-hetarylacrylonitriles (IIIa-IIIv). b. General procedure: A mixture of 10 mmol of acrylic acid thioamide VII and 10 mmol of α-bromoketone II in 25 mL of DMF was stirred at 20°C for 30 min and then left standing for 24 h. The reaction mixture was diluted with an equal volume of water, and the resulting precipitate was filtered off.
71% In N,N-dimethyl-formamide at 80 - 90℃; for 0.333333h;
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