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Issue 21, 2018
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Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides

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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

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Publication details

The article was received on 19 Feb 2018, accepted on 26 Apr 2018 and first published on 26 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00434J
Citation: Org. Biomol. Chem., 2018,16, 3947-3951
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    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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