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Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides

Berezin, Andrey A., Zissimou, Georgia, Constantinides, Christos P., Beldjoudi, Yassine, Rawson, Jeremy M. and Koutentis, Panayiotis A. 2014. Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides. Journal of Organic Chemistry 79 (1) , pp. 314-327. 10.1021/jo402481t

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A two-step route to 1,3-disubstituted benzo- and pyrido-fused 1,2,4-triazinyl radicals is presented. The route involves the N′-(2-nitroarylation) of easily prepared N′-(het)arylhydrazides via nucleophilic aromatic substitution of 1-halo-2-nitroarenes, which in most cases gives N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides in good yields. Mild reduction of the nitro group followed by an acid-mediated cyclodehydration gives the fused triazines, which upon alkali treatment afford the desired radicals. Fifteen examples of radicals are presented bearing a range of substituents at N-1, C-3, and C-7, including the pyrid-2-yl and 8-aza analogues. This route to the N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides, which works well with benzo- and picolinohydrazides, required a modification for aceto- and trifluoroacetohydrazides that involved a multistep synthesis of asymmetrically 1,1-diaryl-substituted hydrazines.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 24 Jan 2020 12:00

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