An efficient synthesis of novel pyridothieno-fused thiazolo[3,2-a]pyrimidinones via Pictet-Spengler reaction

被引：16

作者：

Wang, Dao-Lin ^{[1
]}

Wang, Dong ^{[1
]}

Yan, Liang ^{[1
]}

Pan, Guang-Yu ^{[1
]}

Yang, Jian-Nan ^{[1
]}

机构：

[1] Bohai Univ, Coll Chem & Chem Engn, Liaoning Key Lab Synth & Applicat Funct Compound, Jinzhou 121003, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2016年 / 27卷 / 06期

关键词：

7-Chloromethyl-5H-thiazolo[3,2-a]pyrimidin-5-one; 3-Cyanopyridine-2-thione; Pyrido[3 '',2 '':4 ',5 ']thieno[3 ',2 ':2,3]pyrido [4,5:d] [1,3]Thiazolo[3,2-a]pyrimidine-4-one; Thorpe-Ziegler reaction; Pictet-Spengler reaction; ONE-POT SYNTHESIS; THIAZOLOPYRIMIDINE DERIVATIVES; PYRIMIDINE;

D O I：

10.1016/j.cclet.2016.02.007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the synthesis of novel pyrido[3 '',2 '':4',5']thieno[3',2':2,3]pyrido [4,5:d][1,3]thiazolo[3,2-a]pyrimidine-4-one derivatives (5) has been developed using a Pictet-Spengler reaction between 2-(3-aminothieno[2,3-b]pyridin-2-yl)thiazolo[3,2-a] pyrimidin-5-one (3), which could be obtained from the condensation of 7-(chloromethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one (1) with 3-cyanopyridine-2-thione (2) via Thorpe-Ziegler isomerization, and aromatic aldehydes under NH2SO3H as catalysis in good yields. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：953 / 956

页数：4

共 28 条

[21] Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives [J].