A Multicomponent Approach toward Angularly Fused/Linear Bitriazoles: A Cascade Cornforth Rearrangement and Triazolization

Veettil, Santhini Pulikkal; Parambil, Shandev Pookkandam; Van Hoof, Max; Dehaen, Wim

doi:10.1021/acs.joc.0c03014

A Multicomponent Approach toward Angularly Fused/Linear Bitriazoles: A Cascade Cornforth Rearrangement and Triazolization

Author:

Veettil, Santhini Pulikkal

Parambil, Shandev Pookkandam ; Van Hoof, Max ; Dehaen, Wim

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, C14/19/078#55221580, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A multicomponent reaction of triazoloketones, primary amines, and 4-nitrophenyl azide was developed for the synthesis of hitherto unknown angularly fused/linear bitriazoles. The two-stage mechanism was well proven by the isolation of the intermediate. This sequential reaction consists of Cornforth rearrangement and triazolization, which has also been demonstrated in a one-pot manner.