A simple route to polysubstituted indoles exploiting azide induced furan ring opening

Vladimir T Abaev; Anastasiya T Plieva; Petrakis N Chalikidi; Maxim G Uchuskin; Igor V Trushkov; Alexander V Butin

doi:10.1021/ol5018504

A simple route to polysubstituted indoles exploiting azide induced furan ring opening

Org Lett. 2014 Aug 15;16(16):4150-3. doi: 10.1021/ol5018504. Epub 2014 Aug 1.

Authors

Vladimir T Abaev¹, Anastasiya T Plieva, Petrakis N Chalikidi, Maxim G Uchuskin, Igor V Trushkov, Alexander V Butin

Affiliation

¹ Department of Chemistry, North-Ossetian State University , Vatutina 46, Vladikavkaz 362025, Russian Federation.

PMID: 25084226
DOI: 10.1021/ol5018504

Abstract

A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Aminopyridine / analogs & derivatives
4-Aminopyridine / chemistry
Cyclization
Furans / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Vinyl Compounds / chemistry

Substances

Furans
Indoles
Vinyl Compounds
4-Aminopyridine
4-dimethylaminopyridine