A convenient approach for the preparation of imidazo[1,2-a]-fused bicyclic frameworks via IBX/NIS promoted oxidative annulation

Zsófia Makra; László G. Puskás; Iván Kanizsai

doi:10.1039/C9OB01708A

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A convenient approach for the preparation of imidazo[1,2-a]-fused bicyclic frameworks via IBX/NIS promoted oxidative annulation†

Zsófia Makra,^a László G. Puskás^a and Iván Kanizsai

*^a

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* Corresponding authors

^a AVIDIN Ltd., Alsó kikötő sor 11/D, Szeged, Hungary
E-mail: i.kanizsai@avidinbiotech.com
Fax: +36-62/202108
Tel: +36-62/202107

Abstract

An IBX/NIS-induced intramolecular oxidative annulation of Mannich-type substrates is reported. This metal-free approach involving iodination, NH-oxidation, intramolecular C–N bond formation, and retro-Claisen–Schmidt sequence provides the construction of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine as well as imidazo[1,2-a]pyrazine frameworks with yields up to 93%. In addition, a sequential one-pot process is also presented.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01708A
Article type: Paper
Submitted: 02 Aug 2019
Accepted: 21 Sep 2019
First published: 27 Sep 2019

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Org. Biomol. Chem., 2019,17, 9001-9007

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A convenient approach for the preparation of imidazo[1,2-a]-fused bicyclic frameworks via IBX/NIS promoted oxidative annulation

Z. Makra, L. G. Puskás and I. Kanizsai, Org. Biomol. Chem., 2019, 17, 9001 DOI: 10.1039/C9OB01708A

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Organic & Biomolecular Chemistry

A convenient approach for the preparation of imidazo[1,2-a]-fused bicyclic frameworks via IBX/NIS promoted oxidative annulation†

Abstract

Supplementary files

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A convenient approach for the preparation of imidazo[1,2-a]-fused bicyclic frameworks via IBX/NIS promoted oxidative annulation

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