Issue 12, 2003

Thermal oligomerisation of aryl isocyanides: formation of pyrazino[1,2-a:4,5-a′]diindoles and indigo diarylimines

Abstract

The aryl isocyanides 1–4 are converted at 150 °C into the hexameric pyrazino[1,2-a:4,5-a′]diindoles 15–19. 4-Fluorophenyl isocyanide, when heated at 135 °C, gave the hexamer 19 and the tetrameric indigo di-arylimine 9, and when kept at ambient temperature gave mainly the tetramer 9 in low yield. The structures of the hexamer 19 and the tetramer 9 were established by X-ray crystallography. Mechanisms are proposed for the oligomerisation reactions.

Graphical abstract: Thermal oligomerisation of aryl isocyanides: formation of pyrazino[1,2-a:4,5-a′]diindoles and indigo diarylimines

Supplementary files

Article information

Article type
Paper
Submitted
03 Mar 2003
Accepted
06 May 2003
First published
20 May 2003

Org. Biomol. Chem., 2003,1, 2168-2172

Thermal oligomerisation of aryl isocyanides: formation of pyrazino[1,2-a:4,5-a′]diindoles and indigo diarylimines

J. C. A. Boeyens, L. M. Cook, Y. Ding, M. A. Fernandes and D. H. Reid, Org. Biomol. Chem., 2003, 1, 2168 DOI: 10.1039/B302340K

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