Home Cart 0 Sign in  

[ CAS No. 50329-91-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 50329-91-4
Chemical Structure| 50329-91-4
Structure of 50329-91-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 50329-91-4 ]

Related Doc. of [ 50329-91-4 ]

Alternatived Products of [ 50329-91-4 ]

Product Details of [ 50329-91-4 ]

CAS No. :50329-91-4 MDL No. :MFCD00179896
Formula : C10H5ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 208.60 Pubchem ID :-
Synonyms :

Safety of [ 50329-91-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 50329-91-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 50329-91-4 ]

[ 50329-91-4 ] Synthesis Path-Downstream   1~63

  • 1
  • [ 1076-38-6 ]
  • [ 33513-42-7 ]
  • [ 17831-88-8 ]
  • [ 50329-91-4 ]
YieldReaction ConditionsOperation in experiment
1: 72% 2: 20% Stage #1: 4-hydroxy[1]benzopyran-2-one; N,N-dimethyl-formamide With trichlorophosphate at -10 - 60℃; for 3h; Stage #2: With water at 0℃;
1: 72% 2: 20% With trichlorophosphate at -10 - 60℃;
With trichlorophosphate 1) CHCl3, r.t., 2 h, 2) 50 to 55 deg C, 3 h; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With trichlorophosphate 1) CHCl3, r.t., 2 h, 2) 50 to 55 deg C, 3 h; Yield given. Multistep reaction;

  • 2
  • [ 3289-19-8 ]
  • [ 50329-91-4 ]
  • 4-[(2-methyl-[1,3]dioxolan-2-ylmethyl)-amino]-2-oxo-2<i>H</i>-chromene-3-carbaldehyde [ No CAS ]
  • 3
  • [ 4388-98-1 ]
  • [ 50329-91-4 ]
  • [ 402561-41-5 ]
YieldReaction ConditionsOperation in experiment
93 % Spectr. In chloroform at 20℃; for 2h;
  • 4
  • [ 50329-91-4 ]
  • [ 5325-64-4 ]
  • 2-[(3-formyl-2-oxo-2<i>H</i>-chromen-4-yl)-methyl-amino]-acetamide [ No CAS ]
  • 5
  • [ 50329-91-4 ]
  • [ 25808-30-4 ]
  • 1-methyl-4-oxo-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carbonitrile [ No CAS ]
  • 6
  • [ 50329-91-4 ]
  • [ 25808-30-4 ]
  • 1-methyl-4-oxo-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carbonitrile [ No CAS ]
  • [(3-formyl-2-oxo-2<i>H</i>-chromen-4-yl)-methyl-amino]-acetonitrile [ No CAS ]
  • 7
  • [ 50329-91-4 ]
  • [ 636-99-7 ]
  • 4-chloro-3-[{2-(4-nitrophenyl)hydrazono}methyl]-2Hchromen-2-one [ No CAS ]
  • 8
  • [ 50329-91-4 ]
  • [ 33906-30-8 ]
  • 2-(2-hydroxycarbonylphenyl)[1]benzopyrano[4,3-c]pyrazol-4(2H)-one [ No CAS ]
  • 9
  • [ 50329-91-4 ]
  • [ 33906-30-8 ]
  • 2-[<i>N</i>'-(4-chloro-2-oxo-2<i>H</i>-chromen-3-ylmethylene)-hydrazino]-benzoic acid [ No CAS ]
  • 10
  • [ 50329-91-4 ]
  • [ 51169-05-2 ]
  • 2-(2-pyridyl)[1]benzopyrano[4,3-c]pyrazol-4(2H)-one [ No CAS ]
  • 11
  • [ 50329-91-4 ]
  • [ 40594-29-4 ]
  • 2-(2,4-difluorophenyl)[1]benzopyrano[4,3-c]pyrazol-4(2H)-one [ No CAS ]
  • 12
  • [ 50329-91-4 ]
  • [ 40594-29-4 ]
  • 4-chloro-3-[(2,4-difluoro-phenyl)-hydrazonomethyl]-chromen-2-one [ No CAS ]
  • 13
  • [ 6281-42-1 ]
  • [ 50329-91-4 ]
  • C15H15N3O4 [ No CAS ]
  • 14
  • [ 50329-91-4 ]
  • [ 24644-08-4 ]
  • C22H25NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol for 0.0833333h; Heating;
  • 15
  • [ 50329-91-4 ]
  • [ 22198-72-7 ]
  • 4-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-ylamino)-2-oxo-2H-chromene-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol for 0.0833333h; Heating;
  • 16
  • [ 50329-91-4 ]
  • [ 32654-45-8 ]
  • 3-[(pyridin-2-yl)amino]methylidene}-3,4-dihydro-2H-1-benzopyran-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol for 0.0833333h; Heating;
  • 17
  • [ 4214-74-8 ]
  • [ 50329-91-4 ]
  • C15H8Cl2N2O3 [ No CAS ]
  • 18
  • [ 4815-30-9 ]
  • [ 50329-91-4 ]
  • C21H19NO7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine In ethanol for 0.0833333h; Heating;
  • 19
  • [ 50329-91-4 ]
  • [ 20265-97-8 ]
  • 4-(4-methoxy-phenylamino)-2-oxo-2<i>H</i>-chromene-3-carbaldehyde [ No CAS ]
  • 20
  • [ 50329-91-4 ]
  • [ 41784-08-1 ]
  • C18H13NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol for 0.0833333h; Heating;
  • 21
  • [ 50329-91-4 ]
  • [ 6048-29-9 ]
  • 4‑chloro‑3‑[(1E)‑3‑oxo‑3‑phenyl‑1‑propen‑1‑yl]‑2H‑chromen‑2‑one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 4-chloro-3-formylcoumarin With sodium ethanolate In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: triphenylphenacylphosphonium bromide In toluene at 20℃; for 12h;
  • 22
  • [ 72235-51-9 ]
  • [ 50329-91-4 ]
  • [ 1229011-33-9 ]
YieldReaction ConditionsOperation in experiment
90% In water at 20℃; for 4h;
  • 23
  • [ 269726-49-0 ]
  • [ 50329-91-4 ]
  • [ 1338214-75-7 ]
YieldReaction ConditionsOperation in experiment
40% With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100 - 120℃; Inert atmosphere; Pressure tube; regioselective reaction; 4.2. General procedure for the synthesis of compounds 8-10 General procedure: Coumarin 2a or 2b (2 mmol) and the corresponding aminoheterocycle (2.2 mmol) were placed in a pressure tube under the flow of dry argon and dissolved in dry DMF (10 mL) containing 1 mL of TMSCl. The mixture was heated at 100-120 °C during 2-12 h (controlled by TLC). Then this solution was evaporated under reduced pressure, treated with water, filtered, and dried on the air and recrystallized from an appropriate solvent, or was subjected to a column chromatography over silica gel.
  • 24
  • [ 50329-91-4 ]
  • [ 1118-84-9 ]
  • [ 1343474-05-4 ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; In tetrahydrofuran; at 50℃; for 8h; General procedure: To a solution of 1 (0.100 g, 0.5 mmol) in THF (10 mL) was added K2CO3 (0.140 g, 2.0 equiv). To the stirred solution was dropwise added the 1,3-dicarbonyl compound (2.0 equiv). The reaction mixture was allowed to stir at 50 C and was monitored by TLC. After the complete consummation of the starting material 1, the reaction mixture was acidified using hydrochloric acid (1 M) and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, heptanes/EtOAc).
  • 25
  • [ 50329-91-4 ]
  • [ 41051-15-4 ]
  • [ 1343474-12-3 ]
YieldReaction ConditionsOperation in experiment
77% With potassium carbonate; In tetrahydrofuran; at 50℃; for 6h; General procedure: To a solution of 1 (0.100 g, 0.5 mmol) in THF (10 mL) was added K2CO3 (0.140 g, 2.0 equiv). To the stirred solution was dropwise added the 1,3-dicarbonyl compound (2.0 equiv). The reaction mixture was allowed to stir at 50 °C and was monitored by TLC. After the complete consummation of the starting material 1, the reaction mixture was acidified using hydrochloric acid (1 M) and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, heptanes/EtOAc).
  • 26
  • [ 50329-91-4 ]
  • [ 22502-03-0 ]
  • [ 1343474-04-3 ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate; In tetrahydrofuran; at 50℃; for 8h; General procedure: To a solution of 1 (0.100 g, 0.5 mmol) in THF (10 mL) was added K2CO3 (0.140 g, 2.0 equiv). To the stirred solution was dropwise added the 1,3-dicarbonyl compound (2.0 equiv). The reaction mixture was allowed to stir at 50 C and was monitored by TLC. After the complete consummation of the starting material 1, the reaction mixture was acidified using hydrochloric acid (1 M) and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, heptanes/EtOAc).
  • 27
  • [ 50329-91-4 ]
  • [ 3249-68-1 ]
  • [ 1343474-10-1 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In tetrahydrofuran at 50℃; for 5h; regioselective reaction; General procedure for the cyclocondensation reactions: General procedure: To a solution of 1 (0.100 g, 0.5 mmol) in THF (10 mL) was added K2CO3 (0.140 g, 2.0 equiv). To the stirred solution was dropwise added the 1,3-dicarbonyl compound (2.0 equiv). The reaction mixture was allowed to stir at 50 °C and was monitored by TLC. After the complete consummation of the starting material 1, the reaction mixture was acidified using hydrochloric acid (1 M) and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, heptanes/EtOAc).
  • 28
  • [ 50329-91-4 ]
  • [ 4519-40-8 ]
  • [ 1357063-68-3 ]
YieldReaction ConditionsOperation in experiment
92% In methanol; at 20℃; for 0.15h;ultrasound irradiation; General procedure: A solution of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde (1 mmol) and aromatic amine (1.5 mmol) in methanol (5 ml) was taken in a 10 mL reaction vial. After being capped, the vial containing the reaction mixture was kept under continuous ultrasound irradiation. After completion of the reaction (confirmed by TLC), the reaction mixture was concentrated under vacuum. The residue was purified by flash chromatography (n-hexane/ethylacetate 3:1) to afford the desired product.
  • 29
  • [ 50329-91-4 ]
  • [ 3863-11-4 ]
  • [ 1357063-67-2 ]
YieldReaction ConditionsOperation in experiment
96% In ethanol at 20℃; for 0.25h; ultrasound irradiation;
90% In methanol at 20℃; for 0.133333h; ultrasound irradiation; 4.2. General procedure for the preparation of 6H-chromeno[4,3-b]quinolin-6-one (3a-j) General procedure: A solution of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde (1 mmol) and aromatic amine (1.5 mmol) in methanol (5 ml) was taken in a 10 mL reaction vial. After being capped, the vial containing the reaction mixture was kept under continuous ultrasound irradiation. After completion of the reaction (confirmed by TLC), the reaction mixture was concentrated under vacuum. The residue was purified by flash chromatography (n-hexane/ethylacetate 3:1) to afford the desired product.
81% With Amberlyst-15 In ethanol for 2h; Reflux; Inert atmosphere;
  • 30
  • [ 2644-70-4 ]
  • [ 50329-91-4 ]
  • 1H,4H-4-oxo-benzopyrano[4,3-c]pyrazole [ No CAS ]
  • 31
  • [ 50329-91-4 ]
  • [ 39885-50-2 ]
  • [ 1394232-24-6 ]
  • 32
  • [ 50329-91-4 ]
  • [ 614-16-4 ]
  • [ 1395098-22-2 ]
YieldReaction ConditionsOperation in experiment
80% With sodium azide; triethylamine In N,N-dimethyl-formamide at 50 - 60℃; for 4.5h; Representative procedure for the synthesis of tetrazolo[4′,5′:1,6]pyrido[2,3-c]coumarins 5/7/9: General procedure: 4-Chloro-3-formyl coumarin 2 (1 mmol, 208 mg), sodium azide 3 (1.25 mmol, 80 mg) and cyanoacetamide 4a (1.5 mmol, 126 mg) were taken in a round bottom flask. To this were added DMF (5 ml) and one drop of triethylamine. The reaction mixture was stirred with a magnetic stirrer at 50-60 °C for 3 h. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and then poured into water (10 mL) with stirring. A brown coloured solid product appears. The mixture was kept in a refrigerator for 3 h. The solid product was filtered and purified by column chromatography using petroleum ether and ethyl acetate (7:3) as eluent. The structure of the compound was ascertained as 5a from the spectroscopic data and elemental analysis. Yield = 0.203 g (72.24%).
  • 33
  • [ 50329-91-4 ]
  • [ 4640-66-8 ]
  • [ 1395098-23-3 ]
YieldReaction ConditionsOperation in experiment
83% With sodium azide; triethylamine In N,N-dimethyl-formamide at 50 - 60℃; for 3.5h; Representative procedure for the synthesis of tetrazolo[4′,5′:1,6]pyrido[2,3-c]coumarins 5/7/9: General procedure: 4-Chloro-3-formyl coumarin 2 (1 mmol, 208 mg), sodium azide 3 (1.25 mmol, 80 mg) and cyanoacetamide 4a (1.5 mmol, 126 mg) were taken in a round bottom flask. To this were added DMF (5 ml) and one drop of triethylamine. The reaction mixture was stirred with a magnetic stirrer at 50-60 °C for 3 h. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and then poured into water (10 mL) with stirring. A brown coloured solid product appears. The mixture was kept in a refrigerator for 3 h. The solid product was filtered and purified by column chromatography using petroleum ether and ethyl acetate (7:3) as eluent. The structure of the compound was ascertained as 5a from the spectroscopic data and elemental analysis. Yield = 0.203 g (72.24%).
  • 34
  • [ 50329-91-4 ]
  • [ 4592-94-3 ]
  • [ 1395098-24-4 ]
YieldReaction ConditionsOperation in experiment
85% With sodium azide; triethylamine; In N,N-dimethyl-formamide; at 50 - 60℃; for 3.5h; General procedure: 4-Chloro-3-formyl coumarin 2 (1 mmol, 208 mg), sodium azide 3 (1.25 mmol, 80 mg) and cyanoacetamide 4a (1.5 mmol, 126 mg) were taken in a round bottom flask. To this were added DMF (5 ml) and one drop of triethylamine. The reaction mixture was stirred with a magnetic stirrer at 50-60 C for 3 h. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and then poured into water (10 mL) with stirring. A brown coloured solid product appears. The mixture was kept in a refrigerator for 3 h. The solid product was filtered and purified by column chromatography using petroleum ether and ethyl acetate (7:3) as eluent. The structure of the compound was ascertained as 5a from the spectroscopic data and elemental analysis. Yield = 0.203 g (72.24%).
  • 35
  • [ 50329-91-4 ]
  • [ 3672-47-7 ]
  • [ 1395098-25-5 ]
YieldReaction ConditionsOperation in experiment
75% With sodium azide; triethylamine; In N,N-dimethyl-formamide; at 50 - 60℃; for 5h; General procedure: 4-Chloro-3-formyl coumarin 2 (1 mmol, 208 mg), sodium azide 3 (1.25 mmol, 80 mg) and cyanoacetamide 4a (1.5 mmol, 126 mg) were taken in a round bottom flask. To this were added DMF (5 ml) and one drop of triethylamine. The reaction mixture was stirred with a magnetic stirrer at 50-60 C for 3 h. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and then poured into water (10 mL) with stirring. A brown coloured solid product appears. The mixture was kept in a refrigerator for 3 h. The solid product was filtered and purified by column chromatography using petroleum ether and ethyl acetate (7:3) as eluent. The structure of the compound was ascertained as 5a from the spectroscopic data and elemental analysis. Yield = 0.203 g (72.24%).
  • 36
  • [ 50329-91-4 ]
  • [ 84942-40-5 ]
  • [ 1422695-52-0 ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In ethanol at 25℃; for 0.25h; 4.2 General method for the synthesis of chromeno-2,6,9-trioxabicyclo[3,3,1]nonadienes General procedure: To a solution of 4-chloro-3-formylcoumarin 1a (0.5 mmol) in EtOH (2 mL) was added o-hydroxyacetophenones 2a-l (0.5 mmol) and triethylamine (0.5 mmol) then stirred at 25 °C for 15 min. The precipitate obtained was filtered by whatman filter paper, washed with ethanol and dried. Similar procedure was employed in case of substrates 4a-d.
  • 37
  • [ 50329-91-4 ]
  • [ 1450-75-5 ]
  • [ 1422695-46-2 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In ethanol at 25℃; for 0.25h; 4.2 General method for the synthesis of chromeno-2,6,9-trioxabicyclo[3,3,1]nonadienes General procedure: To a solution of 4-chloro-3-formylcoumarin 1a (0.5 mmol) in EtOH (2 mL) was added o-hydroxyacetophenones 2a-l (0.5 mmol) and triethylamine (0.5 mmol) then stirred at 25 °C for 15 min. The precipitate obtained was filtered by whatman filter paper, washed with ethanol and dried. Similar procedure was employed in case of substrates 4a-d.
  • 38
  • [ 50329-91-4 ]
  • [ 637-04-7 ]
  • [ 1448308-09-5 ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid; In methanol; water; at 60℃; for 0.5h; General procedure: Phenylhydrazine hydrochloride 6a (0.160 g,1.1 mmol) in mixture of H2O and AcOH was added to a stirred solution of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde 5a (0.208 g,1.0 mmol) in methanol at 60 °C and the reaction was continued for another 30 min at same temperature. The reactionwas monitored by TLC and an orangeered precipitate formation was observed. After completion of the reaction, the reaction mixture was cooled to room temperature, precipitate was filtered off, and the resulted precipitate was dissolved in ethyl acetate and washed with cold water to remove the acetic acid. The organic layer was separated and dried over Na2SO4, solvent was removed under reduced pressure afforded (E)-4-chloro-3-((2-phenylhydrazono)methyl)-2H-chromen-2-one (7a, 0.275 g) as orange color sold in 92percent yield.
  • 39
  • [ 50329-91-4 ]
  • [ 622-88-8 ]
  • (E)-3-((2-(4-bromophenyl)hydrazono)methyl)-4-chloro-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With acetic acid In methanol; water at 60℃; for 0.5h; General procedure for the preparation of substituted (E)-4-chloro-3-((2-phenylhydrazono)methyl)-2H-chromen-2-ones (7) General procedure: Phenylhydrazine hydrochloride 6a (0.160 g,1.1 mmol) in mixture of H2O and AcOH was added to a stirred solution of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde 5a (0.208 g,1.0 mmol) in methanol at 60 °C and the reaction was continued for another 30 min at same temperature. The reactionwas monitored by TLC and an orangeered precipitate formation was observed. After completion of the reaction, the reaction mixture was cooled to room temperature, precipitate was filtered off, and the resulted precipitate was dissolved in ethyl acetate and washed with cold water to remove the acetic acid. The organic layer was separated and dried over Na2SO4, solvent was removed under reduced pressure afforded (E)-4-chloro-3-((2-phenylhydrazono)methyl)-2H-chromen-2-one (7a, 0.275 g) as orange color sold in 92% yield.
  • 40
  • [ 50329-91-4 ]
  • [ 57-67-0 ]
  • N-carbamimidoyl-4-((4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In ethanol; acetic acid; at 20℃; for 3h; General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r.
  • 41
  • [ 50329-91-4 ]
  • [ 723-46-6 ]
  • 4-((4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% In ethanol; acetic acid; at 20℃; for 3h; General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r.
  • 42
  • [ 50329-91-4 ]
  • [ 127-79-7 ]
  • 4-((4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In ethanol; acetic acid; at 20℃; for 3h; General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r.
  • 43
  • [ 50329-91-4 ]
  • [ 52173-35-0 ]
  • [ 1607002-99-2 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine at 25℃; for 0.25h;
With triethylamine at 25℃; for 0.25h; Green chemistry; General method for the synthesis of 3-acetyl-1-phenyl-1H-chromeno[4,3-b]pyridine-2,5-dione 5a-p General procedure: To a solution of 4-chloro-3-formylcoumarin 1a (0.5 mmol) in PEG-300 (2 mL) was added acetoacetamides 3a (0.5 mmol) and triethylamine (0.5 mmol)then stirred at 25C for 15 min. The precipitate obtained was filtered by Whatman filter paper, washed with water and dried. Similar procedure was employed in case ofsubstrates 5b-p.
  • 44
  • [ 50329-91-4 ]
  • [ 882-36-0 ]
  • [ 1607003-08-6 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine at 25℃; for 0.25h;
80% With triethylamine at 25℃; for 0.25h; Green chemistry; General method for the synthesis of 3-acetyl-1-phenyl-1H-chromeno[4,3-b]pyridine-2,5-dione 5a-p General procedure: To a solution of 4-chloro-3-formylcoumarin 1a (0.5 mmol) in PEG-300 (2 mL) was added acetoacetamides 3a (0.5 mmol) and triethylamine (0.5 mmol)then stirred at 25C for 15 min. The precipitate obtained was filtered by Whatman filter paper, washed with water and dried. Similar procedure was employed in case ofsubstrates 5b-p.
  • 45
  • [ 5792-36-9 ]
  • [ 50329-91-4 ]
  • [ 1614253-77-8 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In ethanol at 20℃; for 0.25h; (I) Synthesis of chromeno [4, 3-d] pyrimidine 3-oxidederivatives (3a-o): General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 46
  • [ 131-56-6 ]
  • [ 50329-91-4 ]
  • [ 1614253-80-3 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; In ethanol; at 20℃; for 0.25h; General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 47
  • [ 3669-41-8 ]
  • [ 50329-91-4 ]
  • [ 1614253-81-4 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine In ethanol at 20℃; for 0.25h; (I) Synthesis of chromeno [4, 3-d] pyrimidine 3-oxidederivatives (3a-o): General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 48
  • [ 487-49-0 ]
  • [ 50329-91-4 ]
  • [ 1627090-71-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol at 20℃; (II) Representative example of intermediate (A) from the reaction of 1and 2h: A solution of 4-chloro-3-formyl coumarin (1 mmol), 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone(2h) (1 mmol) andtriethylamine (1 equivalent) in 5ml ethanol were stirred at room temperature. Awhite precipitate which was formed instantaneously was filtered within30seconds of initiation of the reaction. The precipitate was washed withethanol and dried.4-(3-hydroxy-4-(2-(4-methoxyphenyl)acetyl)phenoxy)-2-oxo-2H-chromene-3-carbaldehyde(A): White solid, mp 162-168 °C; [Found:C, 69.77; H, 4.21. C25H18O7 requires C, 69.76;H, 4.22%]; νmax(KBr) 1723,1708,1682, 1620, 1579, 1482, 1420, 1218,1045 cm-1; δH(400 MHz CDCl3) 9.98 (1 H, s), 8.10-7.91 (2 H, m), 7.90 ( 1H, t, J7.2Hz ), 7.69 (1 H, d, J 6.4Hz), 7.59 (1 H, d, J 6.8Hz), 7.38 (1 H, t, J 6.0Hz),7.20-7.10 (2 H, m), 6.91-6.81 (2H, m), 4.27 (2H, s), 3.70 (3 H, s); δC (100 MHz CDCl3)196.38, 186.45, 163.84, 160.54, 160.44, 157.93, 154.70, 135.76, 131.82, 130.95,130.59, 130.48, 126.88, 125.40, 125.19, 117.13, 115.90, 115.78, 115.21, 113.78,112.37,54.96, 43.68, 39.99, 38.99; LCMS: MH+, 431.
  • 49
  • [ 487-49-0 ]
  • [ 50329-91-4 ]
  • [ 1614253-82-5 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In ethanol at 20℃; for 0.25h; (I) Synthesis of chromeno [4, 3-d] pyrimidine 3-oxidederivatives (3a-o): General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 50
  • [ 50329-91-4 ]
  • [ 41046-67-7 ]
  • [ 1614253-85-8 ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine In ethanol at 20℃; for 0.25h; (I) Synthesis of chromeno [4, 3-d] pyrimidine 3-oxidederivatives (3a-o): General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 51
  • [ 504-15-4 ]
  • [ 50329-91-4 ]
  • [ 1614253-87-0 ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine In ethanol at 20℃; for 0.25h; (I) Synthesis of chromeno [4, 3-d] pyrimidine 3-oxidederivatives (3a-o): General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 52
  • [ 50329-91-4 ]
  • [ 117-39-5 ]
  • [ 1614253-88-1 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine In ethanol at 20℃; for 0.25h; (I) Synthesis of chromeno [4, 3-d] pyrimidine 3-oxidederivatives (3a-o): General procedure: A solution of 4-chloro-3-formyl coumarin (1mmol), resorcinol derivatives (1 mmol) and triethylamine (1 equivalent) in 3ml ethanolwere stirred at room temperature for 15 min. After completion of the reaction,the precipitate obtained was filtered and washed thoroughly with absoluteethanol and re-crystallized from ethanol to afford pure products 3a-o.
  • 53
  • [ 50329-91-4 ]
  • [ 6945-92-2 ]
  • ethyl 4-oxo-[1]benzopyrano[4,3-c]pyrazole-1(4H)acetate [ No CAS ]
  • 54
  • [ 50329-91-4 ]
  • [ 88-05-1 ]
  • 4-(mesitylamino)-2-oxo-2H-chromene-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.8% With triethylamine In ethanol at 20℃; for 12h; Inert atmosphere; 4-(mesitylamino)-2-oxo-2H-chromene-3-carbaldehyde To a flask containing 4-chloro-3-coumarin carbaldehyde (2.80 g, 10.0 mmol) in ethanol (40 mL) was added NEt3 (1.54 mL, 11.0 mmol) followed by the addition of 2,4,6-trimethylaniline (1.54 mL, 11.0 mmol) at room temperature. After 12 hours of stirring, all the volatiles were pumped off and the residue was extracted with toluene to afford a brown oil that was rinsed with hexane (5 mL) to afford a yellow solid. Yield, 2.24 g, 72.8%. 1H-NMR (400 MHz): δ 2.15 (s, 2,6-CH3, 6H), 2.38 (s, 4-CH3, 3H), 6.88 (m, CH-Ph, 1H), 7.00-7.022 (overlapped, CH-Ph and 3,5-C6H2, 3H), 7.31 (d, CH-Ph, 1H, J = 8.4 Hz), 7.52 (m, CH-Ph, 1H), 10.29(s, C(=O)H, 1H), 13.10 (s, NH, 1H). 13C{1H}-NMR (100 MHz): δ 18.0 (2,6-CH3), 20.9 (4-CH3),118.2, 123.8, 125.4, 129.7, 134.5 (CH-Ph), 96.3, 113.7, 133.2, 134.0, 138.5, 154.8, 158.4, 162.5 (tert-C),192.2 (C(=O)H). Anal. Calc. for C19H17NO3: C, 74.25; H, 5.58; N, 4.56. Found: C, 74.12; H, 5.51;N, 4.39.
  • 55
  • [ 50329-91-4 ]
  • [ 13221-86-8 ]
  • N'-[(E)-(4-chloro-2-oxo-2H-1-benzopyran-3-yl)methylidene]-2,4-dihydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% In ethanol at 20℃; for 0.25h; General synthetic procedure for coumarin based hydrazones 4a-e General procedure: A stirred solutionof 4-chlorocoumarin-3-carbaldehyde (2.0 mmol) 23 in 10 mL abs. ethanol was added to asolution of an appropriate hydrazide: 4-chlorobenzohydrazide 3a, furan-2-carbohydrazide 3b4-methoxybenzohydrazide 3c, 4-(dimethylamino)benzohydrazid 3d or 2,4-dihydroxybenzohydrazide 3e (2.0 mmol) in 10 mL abs. ethanol. The reaction mixture wasvigorously stirred for 15 min at room temperature. The solid product formed was collected byfiltration.
  • 56
  • [ 50329-91-4 ]
  • [ 13221-86-8 ]
  • 2-(2,4-dihydroxybenzoyl)[1]chromeno[4,3-c]pyrazol-4(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% In ethanol; dichloromethane at 20℃; for 1h; General synthetic procedure for chromen[4,3-c]pyrazol-4-ones 5b-g General procedure: A stirredsolution of 4-chlorocoumarin-3-carbaldehyde (2.0 mmol) 2 in 5 mL dichloromethane wasadded to a solution of an appropriate hydrazide: furan-2-carbohydrazide 3b, 4-methoxybenzohydrazide 3c, 4-(dimethylamino)benzohydrazid 3d, 2,4-dihydroxybenzohydrazide 3e, or (2.0 mmol) in 15 mL EtOH. The reaction mixture wasvigorously stirred for 15 min to 1 h at room temperature. The solid product formed wascollected by filtration. The residue was dissolved in 5 mL of CH2Cl2 and filtered over 15 g ofsilica gel with 10:1 petroleum ether -EtOAc mixture as an eluent. After eluent evaporation,yellow crystals of the final compounds 5b-g were obtained.
  • 57
  • [ 50329-91-4 ]
  • [ 182634-34-0 ]
  • 2-(benzo[d][1,3]dioxol-4-yl)-1-(benzo[d][1,3]dioxol-4-ylmethyl)-1,2-dihydro-5H-chromeno[4,3-d]pyrimidin-5-one [ No CAS ]
  • 58
  • [ 226942-29-6 ]
  • [ 50329-91-4 ]
  • 12-bromo-14b-hydroxy-9,10-dihydro-6H-chromeno[4′,3′:3,4]-pyrrolo[2,1-a]isoquinoline-6,7(14bH)-dione [ No CAS ]
  • 59
  • [ 226942-29-6 ]
  • [ 50329-91-4 ]
  • 10-bromo-12,13-dihydro-6H-chromeno[3′,4′:4,5]pyrrolo[2,1-a]-isoquinolin-6-one [ No CAS ]
  • 60
  • [ 226942-29-6 ]
  • [ 50329-91-4 ]
  • 12-bromo-9,10-dihydro-6H-chromeno[4′,3′:3,4]pyrrolo[2,1-a]-isoquinolin-6-one [ No CAS ]
  • 61
  • [ 50329-91-4 ]
  • [ 140675-42-9 ]
  • 11,13-difluoro-9-methyl-9,14a-epoxybenzo[7,8][1,5]dioxocino[3,2-c]chromen-6(9H)-one [ No CAS ]
  • 62
  • [ 50329-91-4 ]
  • [ 140675-42-9 ]
  • 9,11-difluoro-13-methyl-7,13-dihydro-6H-7,13-epoxybenzo[6,7][1,5]dioxocino[3,2-c]chromen-6-one [ No CAS ]
  • 63
  • [ 1450-76-6 ]
  • [ 50329-91-4 ]
  • 13-methyl-11-nitro-7,13-dihydro-6H-7,13-epoxybenzo[6,7][1,5]dioxocino[3,2-c]chromen-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine In ethanol at 20℃; for 2h;
Same Skeleton Products
Historical Records