An efficient method for the synthesis of thieno[3',2':2,3]pyrido-[4,5-d]-thiazolo[3,2-a]pyrimidinones  

作　　者：Dao-Lin Wang Dong Wang Jin-Juan Xing Jian-Hua Qian 

机构地区：[1]College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bahai University, Jinzhou 121003, China

出　　处：《Chinese Chemical Letters》2017年第3期579-582,共4页中国化学快报（英文版）

基　　金：partially supported by innovation team project of Liaoning Province Education Department(No.2015001)

摘　　要：An efficient method for the preparation of thieno[3＇,2＇：2,3]pyrido[4,5-d]thiazolo[3,2-a] pyrimidin-5-ones 5 is described. The key intermediate, 7-（3-amino-4-cyano-5-phenyl aminothieno-2-yl）-5H-thiazolo-[80_TD$IF]3,2-a]pyrimidin-5-one（3）, was synthesized from 7-chloromethyl-5H-thiazolo[3,2-a]pyrimidin-5-one（1）with potassium-（2,2-dicyano-1-phenylaminoethen-1-yl）thiolate（2） by Thorpe–Ziegler isomerization.Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet–Spengler reaction provided thieno-pyridine fused thiazolo[3,2-a]pyrimidines under p-Ts OH as catalyst in good yields.An efficient method for the preparation of thieno[3＇,2＇：2,3]pyrido[4,5-d]thiazolo[3,2-a] pyrimidin-5-ones 5 is described. The key intermediate, 7-（3-amino-4-cyano-5-phenyl aminothieno-2-yl）-5H-thiazolo-[80_TD$IF]3,2-a]pyrimidin-5-one（3）, was synthesized from 7-chloromethyl-5H-thiazolo[3,2-a]pyrimidin-5-one（1）with potassium-（2,2-dicyano-1-phenylaminoethen-1-yl）thiolate（2） by Thorpe–Ziegler isomerization.Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet–Spengler reaction provided thieno-pyridine fused thiazolo[3,2-a]pyrimidines under p-Ts OH as catalyst in good yields.

关 键 词：Thiazolo[3 2-a]pyrimidinone Thienopyridothiazolo[3 2-a]pyrimidinone Thorpe–Ziegler isomerization Pictet–Spengler reaction 

分 类 号：O626[理学—有机化学]