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  1. Home
  2. Indian Institute of Technology Madras
  3. Publication5
  4. Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides
 
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Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides

Date Issued
01-01-2018
Author(s)
Chinta, Bhavani Shankar
Sanapa, Harikrishna
Vasikarla, Kamala Prasad
Baire, Beeraiah
DOI
10.1039/c8ob00434j
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.
Volume
16
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