Synthesis of 1,3-thiazines by a three-component reaction and their transformations into β-lactam-condensed 1,3-thiazine and 1,4-thiazepine derivatives

被引：9

作者：

Peudru, Flavie ^{[1
,2
]}

Lohier, Jean-Francois ^{[1
,2
]}

Gulea, Mihaela ^{[1
,2
,3
]}

Reboul, Vincent ^{[1
,2
]}

机构：

[1] Normandie Univ, Lab Chim Mol & Thioorgan, ENSICAEN, UMR CNRS 6507,INC3M,FR 3038, 6 Bd Marechal Juin, F-14050 Caen, France

[2] Univ Caen Basse Normandie, 6 Bd Marechal Juin, F-14050 Caen, France

[3] Univ Strasbourg, Fac Pharm, Lab Innovat Therapeut, UMR CNRS 7200, 74 Route Rhin BP 24, F-67401 Illkirch Graffenstaden, France

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2016年 / 191卷 / 02期

关键词：

Three-component reaction; 1,3-thiazine; Staudinger reaction; beta-lactam-condensed; 1,4-thiazepine; 1,3-BENZOTHIAZINE DERIVATIVES; RING TRANSFORMATIONS; CYCLIC SULFENAMIDES; ORGANIC-SYNTHESIS; 4,1-BENZOTHIAZEPINES; 1,4-BENZOTHIAZEPINES; CONVERSION; ACCESS;

D O I：

10.1080/10426507.2015.1072191

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Variously substituted 1,3-thiazines have been prepared by a three-component reaction involving a thioamide, an aldehyde, and an alkene. Two diastereomeric thiazines were transformed by stereoselective Staudinger reaction into the corresponding chloro--lactam-condensed-1,3-thiazines, and one of them was rearranged in basic media to afford a highly substituted 1,4-thiazepine. Several of the obtained compounds (six 1,3-thiazines and one -lactam-condensed-1,3-thiazine) were analyzed by X-ray crystallography, which enabled to assign their spatial arrangement and stereochemistry.

引用

页码：220 / 229

页数：10

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