碘-二甲基亚砜促进新型四环噻唑并[3’,2’:2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮类衍生物的合成（英文）  

Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel Tetracyclic Thiazolo[3’,2’:2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones

作　　者：徐姣 张丽宏[2] 张美琦 刘秀波 马伟[1,2] 唐益鑫[3] 王道林 Xu Jiao;Zhang Lihong;Zhang Meiqi;Liu Xiubo;Ma Wei;Tang Yixin;Wang Daolin(State Key Laboratory of Tree Genetics and Breeding,Northeast Forestry University,Harbin 150040;College of Pharmacy,Heilongjiang University of Chinese Medicine,Harbin 150040;College of Chemistry and Chemical Engineering,Bohai University,Jinzhou 121003)

机构地区：[1]东北林业大学林木遗传育种国家重点实验室,哈尔滨150040 [2]黑龙江中医药大学药学院,哈尔滨150040 [3]渤海大学化学化工学院,锦州121003

出　　处：《有机化学》2019年第10期2808-2812,共5页Chinese Journal of Organic Chemistry

摘　　要：介绍了在碘-二甲基亚砜(I2-DMSO)促进作用下,通过Pictet-Spengler反应合成噻唑并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮(5)衍生物的合成方法.该反应的关键中间体2-(3-氨基-5-苯氨基噻唑-2-基)-4H-吡啶[1,2-a]嘧啶-4-酮(3),由2-氯甲基-4H-吡啶[1,2-a]嘧啶-4-酮(1)与N-苯基-N'-氰基-咪唑硫代碳酸钾(2)通过Thorpe-Ziegler异构化反应制得.该合成方法反应条件温和,操作简单,收率高.An iodine-dimethyl sulfoxide(I2-DMSO)promoted efficient method is described for the synthesis of thiazolo-[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidin-5-ones(5)via Pictet-Spengler cyclization.The key intermediate,2-(3-amino-5-phenylaminothiazolo-2-yl)-4H-pyrido[1,2-a]pyrimidin-4-one(3),was readily prepared from 2-chloromethyl-4H-pyrido-[1,2-a]pyrimidin-4-one(1)and potassium N-phenyl-N'-cyano-imido-thiocarbonate(2)by Thorpe-Ziegler isomerization.The novel synthetic method offers the advantage of mild reaction conditions,operational simplicity and higher yields.

关 键 词：吡啶[1 2-a]嘧啶 噻唑并吡啶 Thorpe-Ziegler异构化 Pictet-Spengler反应 I2-DMSO 

分 类 号：O62[理学—有机化学]