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
19 feb 2018
Accepted
26 apr 2018
First published
26 apr 2018

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

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