Studies with enaminones and enaminonitriles: synthesis of 3-aroyl and 3-heteroaroyl-pyrazolo-[1, 5-a] pyrimidines

KD Khalil, HM Al-Matar, M Doa'a, MH Elnagdi

Index: Khalil, Khaled D.; Al-Matar, Hamad M.; Al-Dorri, Doa'a M.; Elnagdi, Mohamed H. Tetrahedron, 2009 , vol. 65, # 45 p. 9421 - 9427

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Citation Number: 26

Abstract

The reaction of electron rich aromatics with cyanoacetic acid and acetic anhydride afforded 3-oxoalkanenitriles. Indium trichloride was used as a Lewis acid catalyst when the aromatic ring was not sufficiently reactive. The synthesized 3-oxoalkanenitriles were subsequently condensed with dimethylformamide dimethylacetal (DMFDMA) to yield enaminones that reacted readily with hydrazine hydrate to yield 4-aroylpyrazole-3-amines. The 4- ...