One-Pot Synthesis of Pyrrolo[2,1-a]isoquinoline-1-carboxamide Derivatives via a Four-Component Reaction

Abdolali Alizadeh; Nasrin Zohreh

doi:10.1055/s-2008-1032033

PAPER

One-Pot Synthesis of Pyrrolo[2,1-a]isoquinoline-1-carboxamide Derivatives via a Four-Component Reaction

Abdolali Alizadeh*, Nasrin Zohreh
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 18716, 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 1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxamide derivatives is described. This involves reaction of N-alkyl-3-oxobutanamides, which result from the addition of amines to diketene, and dibenzoylacetylene in the presence of isoquinoline. The reactive 1:1 intermediate obtained from the addition of isoquinoline to dibenzoyl-acetylene is trapped by OH acids such as N-alkyl-3-oxobutanamides to produce the pyrrolo[2,1-a]isoquinoline-1-carboxamide derivatives.

Key words

amine - diketene - dibenzoylacetylene - isoquinoline - multicomponent reaction - pyrroloisoquinoline

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