Selective Synthesis of 3-Arylbenzo-1,2,3-triazin-4(3H)-ones and 1-Aryl-(1H)-benzo-1,2,3-triazoles from 1,3-Diaryltriazenes through Pd(0) Catalyzed Annulation Reactions

Attoor Chandrasekhar and Sethuraman Sankararaman*

*Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India, Email: sankaiitm.ac.in

A. Chandrasekhar, S. Sankararaman, J. Org. Chem., 2017, 82, 11487-11493.

DOI: 10.1021/acs.joc.7b02023

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Abstract

A Pd(0) catalyzed carbonylative annulation reaction of 1-(2-iodophenyl)-3-aryltriaz-1-enes gave the corresponding 3-arylbenzo-1,2,3-triazin-4(3H)-ones with high selectivity and in excellent yields in the presence of 1 atm of carbon monoxide, whereas 1-aryl-(1H)-benzo-1,2,3-triazoles are provided in good yields in the presence of catalytic amounts of PPh₃.

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proposed mechanism

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Key Words

1,2,3-benzotriazine-4(3H)-ones

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ID: J42-Y2017