多组份一锅法合成新型2-取代噻唑-4-甲酸衍生物
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摘要
以甲醇为溶剂,以醛、胺、硫代乙酸和3-(二甲氨基)-2-异氰基丙烯酸甲酯为原料,经四组份一锅法反应合成了9个新型的2-取代噻唑-4-甲酸衍生物,产率25%~54%,纯度90.3%~100%,其结构经1H NMR,13C NMR和LC-MS表征。
Nine novel 2-substituted thiazole-4-carboxylic acid derivatives in the yield of 25% ~ 54%with purity of 90. 3% ~ 100% were synthesized by four component one-pot reaction of aldehyde,amine,thioacetic acid and 3-dimethylamino-2-isocyano-acrylic acid methyl ester in methanol. The structures were characterized by1 H NMR,13 C NMR and LC-MS.
Nine novel 2-substituted thiazole-4-carboxylic acid derivatives in the yield of 25% ~ 54%with purity of 90. 3% ~ 100% were synthesized by four component one-pot reaction of aldehyde,amine,thioacetic acid and 3-dimethylamino-2-isocyano-acrylic acid methyl ester in methanol. The structures were characterized by1 H NMR,13 C NMR and LC-MS.
引文
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[2]Teoh D,Ayeni T A,Rubatt J M,et al.Dasatinib(BMS-35482)has synergistic activity with paclitaxel and carboplatin in ovarian cancer cells[J].Gynecol Oncol,2011,121(1):187-192.
[3]Fang B,Zhou C H,Rao X C.Synthesis and biological activities of novel amine-derived bis-azoles as potential antibacterial and antifungal agents[J].Eur J Med Chem,2010,45(9):4388-4398.
[4]Francesco M E D,Dessole G,Nizi E P,et al.Novel macrocyclic inhibitors of hepatitis C NS3/4A protease featuring a 2-amino-1,3-thiazole as a P4 carbamate replacement[J].J Med Chem,2009,52(22):7014-7028.
[5]Rostom S A F,El-Ashmawy I M,Badr M H,et al.Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory,analgesic and antimicrobial agents[J].Bioorg Med Chem,2009,17(2):882-895.
[6]崔胜峰,王艳,吕敬松,等.噻唑类化合物应用研究新进展[J].中国科学:化学,2012,42(8):1105-1131.
[7]王冬梅,孙军勇,商永嘉.氨基噻唑类化合的合成研究进展[J].有机化学,2011,31(7):1136-1143.
[8]竺宁,张志伟,高敏,等.2-取代苯并噻唑类衍生物合成方法研究的新进展[J].有机化学,2013,33:1427-1436.
[9]王超,郑学仿,张前.不同位置取代的噻唑烷-4-羧酸及其衍生物的研究进展[J].有机化学,2010,30(10):1441-1454.
[10]Henkel B,Sax M,Domling A.A new and efficient multicomponent solid-phase synthesis of 2-acylaminomethylthiazoles[J].Tetrahedron Letters,2003,44:3679-3682.
[11]Domling A,Henkel B,Beck B,et al.Convergent multicomponent assembly of 2-acyloxymethyl thiazoles[J].Tetrahedron Letters,2003,44:8947-8950.