期刊
SYNTHESIS-STUTTGART
卷 -, 期 17, 页码 2637-2640出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2007-983814
关键词
alkyl isocyanide; dialkyl acetylenedicarboxyl ate; dibenzoylacetylene; nicotinic acid; isonicotinic acid; multicomponent reaction; zwitterion; nicotinamide; isonicotinamide; Dimroth-type rearrangement
An effective route to functionalized nicotinamide and isonicotinamide derivatives is described. This involves the reaction of nicotinic or isonicotinic acid with acetylenic compounds in the presence of alkyl isocyanides. The reactive 1:1 intermediates obtained from the addition of alkyl isocyanides to dialkyl acetylenedicarboxylates or dibenzoylacetylene was trapped by OH-acids such as nicotinic or isonicotinic acid to produce dialkyl 2-(alkylamino)5-[alkyl(3- or 4-pyridylcarbonyl)amino]-3,4-furandicarboxylate, N'(3)-(alkyl)-N-3-[3,4-dibenzoyl-5-(alkylamino)-2-furyl]nicotinamide, and N-4-(alkyl)-N-4- [3,4-dibenzoyl-5-(alkylamino)-2-furyl]isonicotinamide derivatives.
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