Issue 81, 2013
From the journal:

Chemical Communications

Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones†

Alexander V. Aksenov,*a   Alexander N. Smirnov,a   Nicolai A. Aksenov,a   Inna V. Aksenova,a   Liliya V. Frolova,b   Alexander Kornienko,c   Igor V. Magedov‡b  and  Michael Rubin*d  

* Corresponding authors

a Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation
E-mail: alexaks05@rambler.ru

b Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA

c Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA
E-mail: a_k76@txstate.edu

d Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045, USA
E-mail: mrubin@ku.edu

Abstract

3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.

Graphical abstract: Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones

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Article information

DOI
https://doi.org/10.1039/C3CC45696J
Article type
Communication
Submitted
26 Jul 2013
Accepted
09 Aug 2013
First published
13 Aug 2013

Chem. Commun., 2013,49, 9305-9307

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Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones

A. V. Aksenov, A. N. Smirnov, N. A. Aksenov, I. V. Aksenova, L. V. Frolova, A. Kornienko, I. V. Magedov and M. Rubin, Chem. Commun., 2013, 49, 9305 DOI: 10.1039/C3CC45696J

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