Issue 6, 2017

A concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via an unusual TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement

Abstract

An efficient transition-metal-free cascade reaction has been developed for the facile synthesis of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one derivatives from commercially available isatins and 2-haloaryl isothiocyanates. A preliminary mechanistic study suggested an interrupted Dimroth rearrangement was the key step for the successful transformation.

Graphical abstract: A concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via an unusual TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
24 Nov 2016
Accepted
16 Dec 2016
First published
19 Dec 2016

Chem. Commun., 2017,53, 1056-1059

A concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via an unusual TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement

Z. Zhou, F. Jia, C. Xu, S. Jiang, Y. Wu and A. Wu, Chem. Commun., 2017, 53, 1056 DOI: 10.1039/C6CC09376K

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