Issue 40, 2005
From the journal:

Chemical Communications

Domino Michael addition-carbene rearrangement-cyclization reaction of 1-alkynyl(aryl)-λ3-bromanes with 2-mercapto-1,3-benzazoles

Masahito Ochiai*a  and  Norihiro Tadaa  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan
E-mail: mochiai@ph.tokushima-u.ac.jp
Fax: +81 88 633 9504
Tel: +81 88 633 7281

Abstract

Exposure of 1-alkynyl[p-(trifluoromethyl)phenyl](tetrafluoroborato)-λ3-bromanes to 2-mercaptobenzimidazole or benzothiazole in dichloromethane at 0 °C under argon resulted in a domino Michael addition–carbene rearrangement–cyclization reaction to produce directly tricyclic heterocycles in high yields, whereas the reaction with 2-mercaptobenzoxazole afforded 1-alkynyl sulfides.

Graphical abstract: Domino Michael addition-carbene rearrangement-cyclization reaction of 1-alkynyl(aryl)-λ3-bromanes with 2-mercapto-1,3-benzazoles

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B509269H
Article type
Communication
Submitted
05 Jul 2005
Accepted
22 Aug 2005
First published
14 Sep 2005

Chem. Commun., 2005, 5083-5085

Permissions

Request permissions

Domino Michael addition-carbene rearrangement-cyclization reaction of 1-alkynyl(aryl)-λ3-bromanes with 2-mercapto-1,3-benzazoles

M. Ochiai and N. Tada, Chem. Commun., 2005, 5083 DOI: 10.1039/B509269H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements