There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type
HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic
USD 100+
Accessible (Haz class 3, 4, 5 or 8), International
USD 200+
Structure of 762-21-0 * Storage: {[proInfo.prStorage]}
* 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.
Reference：
[1] Chemische Berichte, 1892, vol. 25, p. 3444
[2] Chemische Berichte, 1893, vol. 26, p. 1720
[3] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2>51, p. 55
2
[ 762-21-0 ]
[ 2450-71-7 ]
[ 2050-22-8 ]
Yield
Reaction Conditions
Operation in experiment
82%
With dihydrogen peroxide In ethanol at 65℃; for 12 h;
Example 1, Synthesis of diethyl pyridine-2,3-dicarboxylate:Propiolamine llg (0.2 mmol), diethyl butyldialate 34 g (0.2 mmol), 100 mL ethanol, about 26 mL & lt; RTI ID = 0.0 & gt;35percent hydrogen peroxide (0.30mmol) was added to the 250ml reaction flask, stirring, heated to 65 ° C for 12 hours, TLCThe reaction solution (petroleum ether: ethyl acetate = 2: 1 by volume) was removed and the diethyl butynoate disappeared. After recovery of ethanol by atmospheric distillation,After addition of 100 ml of water, the mixture was extracted with 50 ml of ethyl acetate, and the organic layer was combined three times (in the upper layer), followed by 50 ml of waterAnd 50 ml of saturated brine. The ethyl acetate was recovered by distillation at atmospheric pressure, followed by distillation under reduced pressure (6 mmHg), collecting 165 -170/6mmHg to obtain 36.6 g of the diethyl pyridine-2,3-dicarboxylate in a yield of 82percent.
With toluene-4-sulfonic acid In 1,2-dichloro-ethane; toluene for 20 h; Reflux
1, ethanol (1. 2g, 26mmol), butyne acid (lg, 8. 77mmol), p-toluenesulfonic acid (30mg, 0. 17mmol) and 1,2-dichloroethane (50 mL) added to a 250mL round-bottomed flask.After refluxing for 12 hours, was added 50mL continue refluxing toluene (with trap) for 8 hours.Concentrated and purified by flash chromatography (eluent PE / EA = 98/2) give purified diethyl butyne (1.35 g of, 91percent yield).
Reference：
[1] Patent: CN103483194, 2016, B, . Location in patent: Paragraph 0045
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 20, p. 4519 - 4523
[3] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2>46, p. 209[4] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2>52, p. 289,326,359,
[5] Chemische Berichte, 1885, vol. 18, p. 2271
[6] Journal of the Chemical Society, 1900, vol. 77, p. 1121
[7] Journal of the American Chemical Society, 1959, vol. 81, p. 5372
[8] Journal of the American Chemical Society, 1951, vol. 73, p. 1988
[9] Journal of the Chemical Society, 1948, p. 697
4
[ 13677-32-2 ]
[ 762-21-0 ]
Reference：
[1] Synthesis, 2008, # 17, p. 2798 - 2804
[2] Helvetica Chimica Acta, 1920, vol. 3, p. 569
2,3-dimethyl-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In ethanol; ethyl acetate; chlorobenzene;
EXAMPLE 9 A mixture of 12.8 g of <strong>[2289-75-0]2-amino-4,5-dimethylthiazole</strong>, 150 ml of ethanol and 17 g of acetylene dicarboxylic acid diethyl ester is heated to approximately 30 C., producing a weakly exothermic reaction. The mixture is left standing overnight, subsequently concentrated in vacuo to dryness and the residue is boiled for 1 hour with 100 ml of chlorobenzene. After concentration by evaporation in vacuo, the residue is treated with ethyl acetate, crystallization occurring. The product is filtered off under suction, washed with ether and dried. The 2,3-dimethyl-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester thus obtained melts at 140 to 142 C.
With potassium carbonate; In ethanol; for 18h;Heating / reflux;
Reference Example 200 Ethyl 1-(2,3-difluorophenyl)-5-hydroxy-1H-pyrazole-3-carboxylate To a solution of <strong>[60481-38-1](2,3-difluorophenyl)hydrazine hydrochloride</strong> (32.6 g) in ethanol (452 mL) were added potassium carbonate (62.5 g) and diethyl but-2-ynedioate (38.5 g), and the mixture was refluxed for 18 hr, and concentrated under reduced pressure. The residue was treated with 2 mol/L hydrochloric acid, and the mixture was extracted twice with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was suspended in diethyl ether, and the obtained solid was collected by filtration, and dried under reduced pressure to give the title compound as a pale-yellow solid (26.0 g, yield 43%). 1H-NMR (DMSO-d6) delta: 1.29 (3H, t, J=7.2 Hz), 4.28 (2H, q, J=7.2 Hz), 5.96 (1H, s), 7.36-7.45 (2H, m), 7.59-7.66 (1H, m), 12.2 (1H, s).
4-Bromo-2-trifluoromethoxy-phenylamine (13 g, 0.05 mol) and But-2-ynedioic acid diethyl ester (10.3 g, 0.12 mol) were dissolved in EtOH (120ml) in a 500 ml round bottom flask and refluxed. The reaction was monitored by LC-MS. 3 h later; 0.3 eq. but-2-ynedioic acid diethyl ester was added. At t = 5h, the reaction mixture was concentrated down to remove the solvent under vacuum, a thick oil was obtained and was used without purification for the next step. MS [M+H]+ = 426.
4-Bromo-2-trifluoromethyl-phenylamine (26 g, 0.11 mol)) and But-2-ynedioic acid diethyl ester (20.7 g, 0.12 mol) were dissolved in MeOH (120ml) in a 500 ml round bottom flask and refluxed. The reaction was monitored by LC-MS. 3 h later; LC-MS showed 4-Bromo-2-trifluoromethyl-phenylamine (15 %) was still present, then 0.1 eq. But-2-ynedioic acid diethyl ester was added after reaction cooling down. 2h later, LC-MS did not shown much progress. The reaction mixture was concentrated down to remove the solvent under vacuum, thick oil was obtained and it was used as crude for the next step. MS [M+H]+ = 411.8 (100%), 409.8 (90%)
General procedure: To a stirred solution of dimethyl acetylenedicarboxylate (0.14 g, 1 mmol) and <strong>[556-90-1]2-imino-1,3-thiazolidin-4-one</strong> (3) (0.118 g, 1 mmol) in anhydrous CH2Cl2 (5 mL) was added dropwise a solution of cyclohexyl isocyanide (0.083 g, 1 mmol) in anhydrous CH2Cl2 (3 mL) at rt over 10 min. The reaction mixture was then stirred for 24 h. The solvent was removed under reduced pressure and the residue purified by silica gel (Merck 230-240 mesh) column chromatography using hexane-EtOAc as eluent to yield 4a.
General procedure: To a stirred solution of dimethyl acetylenedicarboxylate (0.14 g, 1 mmol) and <strong>[556-90-1]2-imino-1,3-thiazolidin-4-one</strong> (3) (0.118 g, 1 mmol) in anhydrous CH2Cl2 (5 mL) was added dropwise a solution of cyclohexyl isocyanide (0.083 g, 1 mmol) in anhydrous CH2Cl2 (3 mL) at rt over 10 min. The reaction mixture was then stirred for 24 h. The solvent was removed under reduced pressure and the residue purified by silica gel (Merck 230-240 mesh) column chromatography using hexane-EtOAc as eluent to yield 4a.
General procedure: To a stirred solution of dimethyl acetylenedicarboxylate (0.14 g, 1 mmol) and <strong>[556-90-1]2-imino-1,3-thiazolidin-4-one</strong> (3) (0.118 g, 1 mmol) in anhydrous CH2Cl2 (5 mL) was added dropwise a solution of cyclohexyl isocyanide (0.083 g, 1 mmol) in anhydrous CH2Cl2 (3 mL) at rt over 10 min. The reaction mixture was then stirred for 24 h. The solvent was removed under reduced pressure and the residue purified by silica gel (Merck 230-240 mesh) column chromatography using hexane-EtOAc as eluent to yield 4a.
With 4-amino-o-xylene; In ethanol; at 20℃; for 8h;
General procedure: A mixture of isatin 1 (1 mmol) and malononitrile (2) (1 mmol) in EtOH (3 mL) was stirred for 15 min then treated with a solution of dialkyl acetylenedicarboxylate 3 (1 mmol) and 3,4-dimethylaniline (1 mmol) in EtOH (1 mL). The mixture was stirred at room temperature for 8 h. After completion of the reaction (TLC, eluent: EtOAc/hexane, 1:2), the mixture was filtered and the precipitate washed with H2O (5 mL) and EtOH (5 mL) to afford the pure product 4.
(4aS,13bS,13cS,17bS)-2,3,5,6-tetraethyl-1,1-dimethyl-1H-benzo[c]isoquinolino[1,2-f]pyrrolo[1,2-a][1,6]naphthyridine-1,1,2,3,5,6(4aH,13bH,13cH,17bH)hexacarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
In dichloromethane; at -10 - 20℃; for 12h;
General procedure: To a stirred solution of 2 (2 mmol) and 3 (2 mmol) in 10 mL of CH2Cl2was added 0.24 mL of isoquinoline (2 mmol) dropwise at 10 8Cover 5 min. The reaction mixture was then allowed to warm toroom temperature and stand for 12 h. The solvent was removedunder reduced pressure, and the residue was purified by silica gel(Merck 230-240 mesh) column chromatography using n-hexane/EtOAc (3:1) mixture as eluent to afford the pure product.
General procedure: A flaskwas charged with 1 (0.32 mmol) andwater (30 mL). Then2 (0.38 mmol) was added to the reaction system. The reaction wasstirred at room temperature for 6 h in air. Then the reaction wasextracted with CH2Cl2 (20 mL) and dried over anhydrous Na2SO4.After the solvent was evaporated in vacuo, the residues were purifiedby column chromatography, eluting with petroleum ether(PE)eEtOAc to afford pure 3.
diethyl 2-(cyclohexylamino)-4,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
In toluene; for 1h;Reflux;
General procedure: To a stirred solution of 1 (1 mmol) and 2 (1 mmol) in 5 mL toluene was added amixture of (3, 1 mmol) in 2 mL toluene. The reaction mixture was heated for 1 h. Thesolvent was removed under reduced pressure, and the residue was purified by columnchromatography (SiO2; n-hexane/AcOEt = 3/1)
diethyl 2-(2,4,4-trimethylpentan-2-ylamino)-4,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%
In toluene; for 1h;Reflux;
General procedure: To a stirred solution of 1 (1 mmol) and 2 (1 mmol) in 5 mL toluene was added amixture of (3, 1 mmol) in 2 mL toluene. The reaction mixture was heated for 1 h. Thesolvent was removed under reduced pressure, and the residue was purified by columnchromatography (SiO2; n-hexane/AcOEt = 3/1)
diethyl 2-(2,6-dimethylphenylamino)-2,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
93%
In toluene; for 1h;Reflux;
General procedure: To a stirred solution of 1 (1 mmol) and 2 (1 mmol) in 5 mL toluene was added amixture of (3, 1 mmol) in 2 mL toluene. The reaction mixture was heated for 1 h. Thesolvent was removed under reduced pressure, and the residue was purified by columnchromatography (SiO2; n-hexane/AcOEt = 3/1)
1,2-diethyl 3,3-dimethyl pyrrolo[1,2-a]quinolone-1,2,3,3(3aH)-tetracarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
In methanol; at 20℃; for 12h;
General procedure: To a stirred solution of dialkylacetylenedicarboxylates(1 mmol) and 3 (1 mmol) in MeOH (5 ml) was added dropwisea mixture of quinoline (1 mmol) in MeOH (3 ml).The mixture was stirred for 12 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (SiO2; hexane/AcOEt 5:1) toafford the pure title compounds.
ethyl 4,8-dioxo-2-phenyl-4,8-dihydropyrano[2,3-f]chromene-10-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
66%
With triphenylphosphine; In N,N-dimethyl-formamide; at 60℃; for 12h;
A mixture of 7-hydroxy flavones 3a-3c (1mmol) and PPh3 (1.5 mmol) in DMF(8 mL) was stirred at room temperature for 10 min.Dialkylacetalynedicarboxylate (1.5 mmol) in DMF was added drop wise in 10 min. The brown solutionthus obtained was heated at 60C for 12 h. Then the reaction mixture was diluted with ice cold water and extracted with CH2Cl2. The organic layer was washedwith brine and dried over Na2SO4. The solvent was evaporated under reduced pressure to give a crude mass. The product was isolated by silica gel (100-200 mesh) column chromatography using EtOAc-Petrolium ether (2 : 8) as an eluent, giving pure solidproducts 4a-4f (65-82%).
diethyl 6-chloro-4-formyl-3,4-dihydro-2H-benzo[b][1,4]thiazine-2,3-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
With water; for 12h;Reflux;
General procedure: To a 100 mL flask containing methanol or ethanol (20 mL) and water (4 mL), benzo[d]thiazole derivatives (1.0 equiv., 10.0 mmol) and dimethyl but-2-ynedioate or diethyl but-2-ynedioate (1.1equiv., 11.0 mmol) were added. The reaction was reflux for about 12 h (monitored by TLC). After the reaction was completed, the solvent was removed and water (100 mL) was added, and the mixture was extracted with ethyl acetate (AcOEt) for three times (3 60 mL). The organic layers were combined, dried with sodium sulphate anhydrous, and filtered. The solvent was removed under the reduced pressure and the residue was purified with silica gel (200-300 m) to afford the target compounds 2aa-ea.
diethyl 2-(cyclohexylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
92%
In acetonitrile; at 20℃; for 24h;
General procedure: A mixture of <strong>[550-24-3]2,5-dihydroxy-6-undecyl-1,4-benzoquinone</strong> (1 mmol), diethylacetylene dicarboxylate (1 mmol) and isocyanides (1 mmol) was stirred in CH3CN (5 mL) at RT for 24 h. The progress of the reaction was monitored by TLC (20% methanol in chloroform). After completion of the reaction, the separated solid was filtered off and washed with hexane. The crude product was purified by recrystallization from ethanol to give 4.
diethyl 2-(tert-butylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
In acetonitrile; at 20℃; for 24h;
General procedure: A mixture of <strong>[550-24-3]2,5-dihydroxy-6-undecyl-1,4-benzoquinone</strong> (1 mmol), diethylacetylene dicarboxylate (1 mmol) and isocyanides (1 mmol) was stirred in CH3CN (5 mL) at RT for 24 h. The progress of the reaction was monitored by TLC (20% methanol in chloroform). After completion of the reaction, the separated solid was filtered off and washed with hexane. The crude product was purified by recrystallization from ethanol to give 4.
diethyl 2-(2,6-dimethylphenylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
In acetonitrile; at 20℃; for 24h;
General procedure: A mixture of <strong>[550-24-3]2,5-dihydroxy-6-undecyl-1,4-benzoquinone</strong> (1 mmol), diethylacetylene dicarboxylate (1 mmol) and isocyanides (1 mmol) was stirred in CH3CN (5 mL) at RT for 24 h. The progress of the reaction was monitored by TLC (20% methanol in chloroform). After completion of the reaction, the separated solid was filtered off and washed with hexane. The crude product was purified by recrystallization from ethanol to give 4.
(E)-diethyl 2,3-bis(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)fumarate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
63%
With 4,4'-bipyridine; In tetrahydrofuran; at 60℃; for 14h;Inert atmosphere; Sealed tube;
In a glove box, a glass tube having PTFE stopcock (J. Young),equipped with a magnetic stirring bar, was charged with 9e (1.7 mg, 0.010 mmol), 11 (58 mg,0.23 mmol), THF (0.2 mL), and 7a (34 mg, 0.20 mmol). The tube was sealed by the stopcock and was taken out from the glove box. The mixture was heated at 60 °C with stirring for 14 h.After cooling to room temperature, the volatiles were removed from the reaction mixture under reduced pressure. The residue was purified by column chromatography on silica gel(CHROMATOREX DIOL, eluent: hexane:CHCl3 = 5:1) to afford (E)-12b (54 mg, 63percent) as awhite solid. Geometry of the carbon?carbon double bond was assigned on the analogy of that of (E)-8a. Diethyl 2,3-bis(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)fumarate [(E)-12b]1H NMR (400 MHz, CDCl3) delta 4.11-4.32 (m, 6H), 1.62-1.79 (m, 4H), 1.34 (s, 6H), 1.27 (t, J =6.8 Hz, 6H), 1.26 (s, 6H), 1.22 (d, J = 6.4 Hz, 6H). 13C NMR (101 MHz, CDCl3) delta 168.9, 150.3(broad, C?B), 71.2, 65.3, 61.0, 45.8, 31.2, 27.54 (either meso or racemate), 27.52 (either mesoor racemate), 23.1, 14.2. 11B NMR (128 MHz, CDCl3) delta 26.1. HRMS (ESI, positive) m/z calcdfor C20H34B2O8Na+ [M + Na]+: 447.2332, found: 447.2332.
General procedure: A suspension of 1,6-disubstituted quinoline-2,4-(1H,3H)-diones 1a-f (1 mmol) in 10 mL absolute ethanol wasadded to a solution of diethyl acetylenedicarboxylate (2a)(0.170 g, 1 mmol) in 15 mL absolute ethanol and 0.5 mLof triethylamine. The reaction mixture was gently refluxedfor 4-8 h, until the reactants had disappeared (monitoredby TLC). The resulting precipitates of 3a-f were filteredoff and dried. The precipitates were recrystallized fromsuitable solvents.
4-cyano-4-(4,5-dihydro-3-methyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)-4,5-dihydro-5-imino-1-(4-propylphenyl)-1H-pyrrole-2,3-dicarboxylic acid 2,3-diethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62%
General procedure: A mixture of 4a (0.213 g, 1.5 mmol) or 4b (0.255 g, 1.5 mmol) and/or 5a (0.093 g, 1 mmol), 5b(0.107 g, 1 mmol), 5c (0.121 g, 1 mmol), 5d (0.135 g, 1 mmol), or 5e (0.123 g, 1 mmol) in EtOH (20 mL) was stirred at rt for 1 h. To the resulting mixture, 1 (0.236 g, 1 mmol), 2 (0.250 g, 1 mmol), or 3 (0.281 g,1 mmol) was added and then the mixture was stirred at rt for 24 h. Further processing of the resultingmixture is described in the following paragraphs.(A) To a reaction mixture, cold H2O was added with stirring. The resulting mixture was extracted withCHCl3 (150 mL). The extract was dried over anhydrous Na2SO4 and concentrated in vacuo. The residuewas recrystallized from acetone/petroleum ether to afford 6a-j and 7a-j.(B) The precipitate was collected by filtration, washed with Et2O, dried, and recrystallized from anappropriate solvent to give 8a-j
4-cyano-4-[4,5-dihydro-3-methyl-1-(4-methylphenyl)-5-oxo-1H-pyrazol-4-yl]-4,5-dihydro-5-imino-1-(4-propylphenyl)-1H-pyrrole-2,3-dicarboxylic acid 2,3-diethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
57%
General procedure: A mixture of 4a (0.213 g, 1.5 mmol) or 4b (0.255 g, 1.5 mmol) and/or 5a (0.093 g, 1 mmol), 5b(0.107 g, 1 mmol), 5c (0.121 g, 1 mmol), 5d (0.135 g, 1 mmol), or 5e (0.123 g, 1 mmol) in EtOH (20 mL) was stirred at rt for 1 h. To the resulting mixture, 1 (0.236 g, 1 mmol), 2 (0.250 g, 1 mmol), or 3 (0.281 g,1 mmol) was added and then the mixture was stirred at rt for 24 h. Further processing of the resultingmixture is described in the following paragraphs.(A) To a reaction mixture, cold H2O was added with stirring. The resulting mixture was extracted withCHCl3 (150 mL). The extract was dried over anhydrous Na2SO4 and concentrated in vacuo. The residuewas recrystallized from acetone/petroleum ether to afford 6a-j and 7a-j.(B) The precipitate was collected by filtration, washed with Et2O, dried, and recrystallized from anappropriate solvent to give 8a-j
4-cyano-4-[4,5-dihydro-3-methyl-1-(4-nitrophenyl)-5-oxo-1H-pyrazol-4-yl]-4,5-dihydro-5-imino-1-(4-propylphenyl)-1H-pyrrole-2,3-dicarboxylic acid 2,3-diethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
67%
General procedure: A mixture of 4a (0.213 g, 1.5 mmol) or 4b (0.255 g, 1.5 mmol) and/or 5a (0.093 g, 1 mmol), 5b(0.107 g, 1 mmol), 5c (0.121 g, 1 mmol), 5d (0.135 g, 1 mmol), or 5e (0.123 g, 1 mmol) in EtOH (20 mL) was stirred at rt for 1 h. To the resulting mixture, 1 (0.236 g, 1 mmol), 2 (0.250 g, 1 mmol), or 3 (0.281 g,1 mmol) was added and then the mixture was stirred at rt for 24 h. Further processing of the resultingmixture is described in the following paragraphs.(A) To a reaction mixture, cold H2O was added with stirring. The resulting mixture was extracted withCHCl3 (150 mL). The extract was dried over anhydrous Na2SO4 and concentrated in vacuo. The residuewas recrystallized from acetone/petroleum ether to afford 6a-j and 7a-j.(B) The precipitate was collected by filtration, washed with Et2O, dried, and recrystallized from anappropriate solvent to give 8a-j
diethyl 5-(4-methylthiazol-5-yl)-1-phenyl-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With manganese(III) triacetate dihydrate; In dimethyl sulfoxide; at 80℃; for 4h;
General procedure: A mixture of aniline (1a, 0.5 mmol), diethyl acetylenedicarboxylate (2a, 0.5mmol), styrene (3a, 0.6 mmol), Mn(OAc)3·2H2O (1.0 mmol, 2.0 equiv), and DMSO(4 mL) in a 25 mL sealed tube was stirred at 80 oC for 4 h. After completion of thereaction, the mixture was diluted with water (30 mL) and extracted with ethyl acetate(3 × 30 mL). The combined organic layers were washed with water and brine, driedS3over anhydrous Na2SO4 and filtered. Then the solvent was removed under reducedpressure to obtain crude product. Further purification by flash columnchromatography on silica gel with EtOAc/petroleum as the eluent gave 4a in 85%yield (155.2 mg).
diethyl 5-(4-methylthiazol-5-yl)-1-phenyl-1H-pyrrole-2,3-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
General procedure: A mixture of aniline (1a, 0.5 mmol), diethyl acetylenedicarboxylate (2a, 0.5 mmol),styrene (3a, 0.6 mmol), Mn(OAc)3·2H2O (1.0 mmol, 2.0 equiv), and DMSO (4 mL)in a 25 mL sealed tube was stirred at 80 oC for 4 h, then K2S2O8 (337.9 mg, 1.25mmol) was added into the reaction mixture and the reaction was monitored by TLC.After completion of the reaction, the mixture was diluted with water (30 mL) andextracted with ethyl acetate (3 × 30 mL). Then the combined organic layers werewashed with water and brine, dried over anhydrous Na2SO4 and filtered. The solventwas removed under reduced pressure to obtain crude product. Further purification byflash column chromatography on silica gel with EtOAc/petroleum as the eluent gave8a in 83% yield (150.7 mg).
diethyl 2-(2-ethoxy-2-oxoethylidene)-5-oxo-7-propyl-2H,4a'H,5H-spiro[thiazolo[3,2-a]pyrimidine-3,3'-[1,3]oxazino[3,2-a]quinoline]-1',2'-dicarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
In toluene; at 110℃; for 5h;
To a stirred solution of 2 (2 mmol) and 3 (1 mmol) in 10 mL of toluene at 110C was added dropwise a solution of isoquinoline or quinoline (0.286 g, 1 mmol) in 4 mL of toluene. After completion of the reaction as monitored by TLC, the solvent was evaporated and the residue was recrystallized from AcOEt/n-hexane (1:3) to afford the pure product.
diethyl 2-(2-ethoxy-2-oxoethylidene)-5-oxo-7-propyl-2H,5H,11b'H-spiro[thiazolo[3,2-a]pyrimidine-3,2'-[1,3]oxazino[2,3-a]isoquinoline]-3',4'-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
In toluene; at 110℃; for 5h;
To a stirred solution of 2 (2 mmol) and 3 (1 mmol) in 10 mL of toluene at 110C was added dropwise a solution of isoquinoline or quinoline (0.286 g, 1 mmol) in 4 mL of toluene. After completion of the reaction as monitored by TLC, the solvent was evaporated and the residue was recrystallized from AcOEt/n-hexane (1:3) to afford the pure product.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
HazMat Fee +
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
