Synthesis of Nicotinamide and Isonicotinamide Derivatives via Multicomponent Reaction of Alkyl Isocyanides and Acetylenic Compounds in the Presence of Nicotinic or Isonicotinic Acid

Abdolali Alizadeh; Qasem Oskueyan; Sadegh Rostamnia

doi:10.1055/s-2007-983814

PAPER

Synthesis of Nicotinamide and Isonicotinamide Derivatives via Multicomponent Reaction of Alkyl Isocyanides and Acetylenic Compounds in the Presence of Nicotinic or Isonicotinic Acid

Abdolali Alizadeh*, Qasem Oskueyan, Sadegh Rostamnia
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;

Abstract

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Abstract

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.

Key words

alkyl isocyanide - dialkyl acetylenedicarboxylate - dibenzoylacetylene - nicotinic acid - isonicotinic acid - multicomponent reaction - zwitterion - nicotinamide - isonicotinamide - Dimroth-type rearrangement

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