Polycyclic heteroaromatics from reactions of acylbenzotriazoles with aryl isocyanates

AR Katritzky; TB Huang; MV Voronkov; PJ Steel

doi:10.1021/jo0009604

Polycyclic heteroaromatics from reactions of acylbenzotriazoles with aryl isocyanates

J Org Chem. 2000 Nov 17;65(23):8069-73. doi: 10.1021/jo0009604.

Authors

AR Katritzky¹, TB Huang, MV Voronkov, PJ Steel

Affiliation

¹ Department of Chemistry, University of Canterbury, Christchurch, New Zealand.

PMID: 11073620
DOI: 10.1021/jo0009604

Abstract

N-Acylbenzotriazoles react with aryl isocyanates to form, depending on the type of acyl group, compounds based on five different classes of polycyclic heteroaromatics. Higher alkanoyl-, acetyl-, acetoacetyl-, aroyl-, and cinnamoylbenzotriazoles yield, respectively, derivatives of quinoline, pyrimidino[5,4-c]quinoline, benzo[b]-1,8-naphthyridine, phenanthridine, and indolo[2, 3-b]quinoline by incorporating 3, 3, 4, 2, and 2 molecules, respectively, of the isocyanate per acylbenzotriazole molecule.