Volume 20, Issue 2
Heterocyclic Compounds
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ChemInform Abstract: Efficient Synthesis of Oligo-N-methylpyrrolecarboxamides and Related Compounds.

E. NISHIWAKI

E. NISHIWAKI

Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan

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S. TANAKA

S. TANAKA

Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan

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H. LEE

H. LEE

Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan

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M. SHIBUYA

M. SHIBUYA

Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan

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First published: January 10, 1989

Abstract

Acylation of 1-methylpyrrole (Ia) and N-methylimidazole (Ib) with trichloroacetyl chloride (II) yields the ketones (III) which produce a mixture of the isomeric nitroheterocycles (V) and (VI) on treatment with nitric acid (IV).

ChemInform Abstract

Acylation of 1-methylpyrrole (Ia) and N-methylimidazole (Ib) with trichloroacetyl chloride (II) yields the ketones (III) which produce a mixture of the isomeric nitroheterocycles (V) and (VI) on treatment with nitric acid (IV). The derivative (Va) couples with alcohols and amines (VII) to give the esters and amides (VIII). The nitropyrrolecarboxamides (VIIIc) and (VIIId) are transformed into the oligopeptides (IX) and (X) by hydrogenation and condensation reaction with the tri- chloromethyl ketone (Va).

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