Synthesis 2015; 47(04): 489-496
DOI: 10.1055/s-0034-1378921
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Heteroarylogous 1H-Indole-3-carboxamidines via a Three-Component Interrupted Ugi Reaction

Fabio La Spisa
a   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale ‘A. Avogadro’, Largo Donegani 2, 28100 Novara, Italy   Fax: +39(0321)375621   eMail: giancesare.tron@unipmn.it
,
Fiorella Meneghetti
b   Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milano, Italy
,
Beatrice Pozzi
a   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale ‘A. Avogadro’, Largo Donegani 2, 28100 Novara, Italy   Fax: +39(0321)375621   eMail: giancesare.tron@unipmn.it
,
Gian Cesare Tron*
a   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale ‘A. Avogadro’, Largo Donegani 2, 28100 Novara, Italy   Fax: +39(0321)375621   eMail: giancesare.tron@unipmn.it
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Publikationsverlauf

Received: 01. September 2014

Accepted after revision: 13. Oktober 2014

Publikationsdatum:
17. November 2014 (online)


Abstract

A novel one-pot multicomponent synthesis of heteroarylogous 1H-indole-3-carboxamidines starting from readily available N-alkyl-N-(1H-indol-2-ylmethyl)amines, isocyanides, and carbonyl compounds is reported. The strategy exploits the ability of the indole nucleus to interrupt the classical Ugi reaction, by intercepting the nascent nitrilium ion.

Supporting Information