Tetrahedron

A short synthesis of phenanthro [2, 3-d] imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles

T Fonseca, B Gigante, TL Gilchrist

Index: Fonseca, Tatiana; Gigante, Barbara; Gilchrist, Thomas L Tetrahedron, 2001 , vol. 57, # 9 p. 1793 - 1799

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Citation Number: 149

Abstract

Methyl cis-deisopropyldehydroabietate was selectively nitrated at the 12-position by reaction with 'claycop', a montmorillonite clay impregnated with copper (II) nitrate. The 12-nitro compound was reduced to the corresponding amine and this was subjected to a combined acylation and ortho nitration. The compounds so produced were further converted into octahydro-1H-phenanthro [2, 3-d] imidazoles by reductive cyclization. The same acylation- ...

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