Microwave-assisted one-pot synthesis of 2-aryl-5,6-dihydro-4H-1,3-thiazines via reaction between Lawesson's reagent and allyl arylamides derived from Morita-Baylis-Hillman acetates

被引：13

作者：

Bhowmik, Subhendu ^{[1
]}

Mishra, Amita ^{[1
]}

Batra, Sanjay ^{[1
]}

机构：

[1] Cent Drug Res Inst, CSIR, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India

来源：

RSC ADVANCES | 2011年 / 1卷 / 08期

关键词：

CONSTRUCTION; HETEROCYCLES; NITROGEN;

D O I：

10.1039/c1ra00362c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot synthesis of 2-aryl-5,6-dihydro-4H-1,3-thiazines from the allyl arylamides afforded from the Morita-Baylis-Hillman acetates of acrylates has been developed. The protocol comprises of Lawesson's reagent-mediated transformation of allyl arylamide to thioamide followed by tandem intramolecular sulfa-Michael reaction under microwave condition to afford the products as a mixture of syn and anti isomers. Based on a plausible mechanism syn and anti-isomers are proposed as the kinetic and thermodynamic products, respectively. Further it has been experimentally demonstrated that the syn isomer is transformed to the anti isomer via prolonged heating.

引用

页码：1464 / 1470

页数：7