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Unexpected O-H Insertion of Rhodium-Azavinylcarbenes with N-Acylhydrazones: Divergent Synthesis of 3,6-Disubstituted- and 3,5,6-Trisubstituted-1,2,4-Triazines

Jiang Meng, Min Wen, Shiwei Zhang, Peiwen Pan, Xingxin Yu* and Wei-Ping Deng*

*Shanghai Key Laboratory of New Drug Design & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China, Email: xxyuecust.edu.cn, weiping_dengecust.edu.cn

J. Meng, M. Wen, S. Zhang, P. Pan, X. Yu, W.-P. Deng, J. Org. Chem., 2017, 82, 1676-1687.

DOI: 10.1021/acs.joc.6b02846 (free Supporting Information)


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Abstract

An unexpected rhodium-catalyzed O-H insertion/rearrangement of N-acylhydrazones with N-sulfonyl-1,2,3-triazoles provides common intermediates for the synthesis of 1,2,4-triazines with different substitution patterns. Subsequent intramolecular cyclization reactions under mild conditions yield 3,6-disubstituted- and 3,5,6-trisubstituted-1,2,4-triazines depending on the conditions.


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Key Words

1,2,4-triazines


ID: J42-Y2017