Synthesis of heteroarylogous 1H-indole-3-carboxamidines via a three-component interrupted Ugi reaction

Fabio La Spisa; Fiorella Meneghetti; Beatrice Pozzi; Gian Cesare Tron

doi:10.1055/s-0034-1378921

Synthesis of heteroarylogous 1H-indole-3-carboxamidines via a three-component interrupted Ugi reaction

Fabio La Spisa
, Fiorella Meneghetti
, Beatrice Pozzi
, Gian Cesare Tron

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	489-496
Number of pages	8
Journal	Synthesis
Volume	47
Issue number	4
DOIs	https://doi.org/10.1055/s-0034-1378921
Publication status	Published - Feb 2015

Keywords

Ugi reaction
indoles
isocyanides
multicomponent reactions
secondary amines

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10.1055/s-0034-1378921

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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.",

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author = "\{La Spisa\}, Fabio and Fiorella Meneghetti and Beatrice Pozzi and Tron, \{Gian Cesare\}",

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AU - Meneghetti, Fiorella

AU - Pozzi, Beatrice

AU - Tron, Gian Cesare

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart · New York.

PY - 2015/2

Y1 - 2015/2

N2 - 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.

AB - 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.

KW - Ugi reaction

KW - indoles

KW - isocyanides

KW - multicomponent reactions

KW - secondary amines

UR - https://www.scopus.com/pages/publications/84922204710

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DO - 10.1055/s-0034-1378921

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JO - Synthesis

JF - Synthesis

IS - 4

ER -

Synthesis of heteroarylogous 1H-indole-3-carboxamidines via a three-component interrupted Ugi reaction

Abstract

Keywords

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