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Modular Synthesis of 3,6-Disubstituted-1,2,4-triazines via the Cyclodehydration of β-Keto-N-acylsulfonamides with Hydrazine Salts

Author:
Dowling, Matthew S., Jiao, Wenhua, Hou, Jie, Jiang, Yuchun, Gong, Shangsheng
Source:
Journal of organic chemistry 2018 v.83 no.7 pp. 4229-4238
ISSN:
1520-6904
Subject:
chemical reactions, chemical structure, hydrazine, organic chemistry, organochlorine compounds, salts
Abstract:
A straightforward method for preparing 3,6-disubstituted-1,2,4-triazines through a redox-efficient cyclodehydration of β-keto-N-acylsulfonamides with hydrazine salts is described. Two approaches for synthesizing the requisite β-keto-N-acylsulfonamides are presented, which allow for the late stage incorporation of either the C3 or C6 substituent in a flexible manner from acid chlorides or α-bromoketones, respectively. The scope of this methodology includes primary and secondary sp³-linked substituents at both the C3 and C6 positions, and the mild reaction conditions tolerate a variety of sensitive functionalities.
Agid:
6047114