Tetrahedron

Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)

C Niu, J Li, TW Doyle, SH Chen

文献索引：Niu, Chuansheng; Li, Jun; Doyle, Terrence W.; Chen, Shu-Hui Tetrahedron, 1998 , vol. 54, # 23 p. 6311 - 6318

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被引用次数: 42

摘要

Palladium-catalyzed cross-coupling of methylboronic acid with 2-chloro-3-nitropyridine produced 2-methyl-3-nitropyridine 4 in one step in high yield. Oxidation of 4 with selenium dioxide gave aldehyde 5. Alternatively, condensation of 4 with DMFDMA followed by oxidation gave 5 in a two step higher yielding conversion. Subsequent direct coupling of 5 with thiosemicarbazide followed by reduction of the nitro group using stannous chloride or ...