Issue 21, 2018

Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides

Abstract

We report an electrophile promoted, highly regioselective (∼100%) synthesis of 5-membered haloimidiates from 2-(1-alkynyl)benzamides under metal free conditions. The steric bulk in association with neighbouring group assistance at the propargylic carbon of an alkyne has been employed as the dictating factor to achieve the regioselectivity. A very broad structural diversity has been observed for propargylic alcohols and acetates, and for amide functional groups. Control experiments supported the role of the steric bulk as well as neighbouring group assistance from the oxygen atom of the substituent for the observed high regioselectivity.

Graphical abstract: Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides

Supplementary files

Article information

Article type
Paper
Submitted
03 جمادى الثانية 1439
Accepted
10 شعبان 1439
First published
10 شعبان 1439

Org. Biomol. Chem., 2018,16, 3947-3951

Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides

B. S. Chinta, H. Sanapa, K. P. Vasikarla and B. Baire, Org. Biomol. Chem., 2018, 16, 3947 DOI: 10.1039/C8OB00434J

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