Carbon-carbon bond formation by radical cyclisation: Regioselective synthesis of coumarin-annulated sulfur heterocycles

被引：28

作者：

Majumdar, KC ^{[1
]}

Biswas, A ^{[1
]}

Mukhopadhyay, PP ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

SYNTHESIS-STUTTGART | 2003年 / 15期

关键词：

heterocyclic compounds; sulfur heterocycles; organotin reagent; 4-sulfanylcoumarin; radical cyclisation; 6-endo-trig;

D O I：

10.1055/s-2003-41068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple convergent synthesis of cis-benzothiopyrano [3,2-c]benzopyran-7(2H)-ones 4a-f (70-75%) through implementation of a regioselective '6-endo-trig' aryl radical cyclisation of the respective 4-[(2-bromobenzyl)sulfanyl]-2H-chromen-2-ones 3a-f (80-85%) with tributyltin hydride in the presence of a radical initiator (AIBN) is described. The starting materials 3a-f are synthesised by phase-transfer-catalysed reaction of 4-sulfanyl-2H-chromen-2-ones la-c with 2-bromobenzyl bromides 2a,b.

引用

页码：2385 / 2389

页数：5

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