期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 1, 页码 314-327出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo402481t
关键词
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资金
- University of Cyprus
- Cyprus Research Promotion Foundation [YGammaEIA/BIOSigma/0308(BIE)/13, NEKYPi/0308/02, ANABAThetaMISigmaH/0308/32]
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)arylN'-[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.
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