Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis and Properties of Nitrosoazulenes
Tetsuo NozoePaw Wang YangHiroshi OgawaTakashi Toda
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1968 Volume 41 Issue 9 Pages 2095-2101

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Abstract

Ethyl 2-amino-3-nitrosoazulene-1-carboxylate (II) was synthesized from ethyl 2-aminoazulene-1-carboxylate by treatment with isoamyl nitrite. The structure of the amino-nitrosoazulene was proved by the reductive acetylation of the azulene to give ethyl 2,3-diacetylaminoazulene-1-carboxylate. This nitrosation method was then applied to several azulenes possessing different substituents; it yielded some stable nitrosoazulene derivatives. The spectral properties of the nitrosoazulenes will be discussed. The condensation reactions of II with aromatic amines failed to give azo-dyes, but with diethyl malonate and malononitril they gave the corresponding pyrazinoazulene derivatives.

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