New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides

Didier Coffinier; Laurent El Kaim; Laurence Grimaud

doi:10.1021/ol8029438

New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides

Didier Coffinier
, Laurent El Kaim
, Laurence Grimaud

Unité Chimie et Procédés

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

Abstract

When allylamine is used as the amino input in Ugi-Smiles couplings of o-nitrophenols, the resulting adducts can be deallylated by a palladiumcatalyzed process leading to a formal Ugi-Smiles coupling with ammonia. This new sequence, combined with hydrogenolysis of the nitro group, offers an interesting multicomponent entry to benzotriazole and benzimidazole scaffolds.

Original language	English
Pages (from-to)	995-997
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	4
DOIs	https://doi.org/10.1021/ol8029438
Publication status	Published - 19 Feb 2009
Externally published	Yes

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10.1021/ol8029438

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title = "New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides",

abstract = "When allylamine is used as the amino input in Ugi-Smiles couplings of o-nitrophenols, the resulting adducts can be deallylated by a palladiumcatalyzed process leading to a formal Ugi-Smiles coupling with ammonia. This new sequence, combined with hydrogenolysis of the nitro group, offers an interesting multicomponent entry to benzotriazole and benzimidazole scaffolds.",

author = "Didier Coffinier and Kaim, \{Laurent El\} and Laurence Grimaud",

year = "2009",

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doi = "10.1021/ol8029438",

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journal = "Organic Letters",

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T1 - New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides

AU - Coffinier, Didier

AU - Kaim, Laurent El

AU - Grimaud, Laurence

PY - 2009/2/19

Y1 - 2009/2/19

N2 - When allylamine is used as the amino input in Ugi-Smiles couplings of o-nitrophenols, the resulting adducts can be deallylated by a palladiumcatalyzed process leading to a formal Ugi-Smiles coupling with ammonia. This new sequence, combined with hydrogenolysis of the nitro group, offers an interesting multicomponent entry to benzotriazole and benzimidazole scaffolds.

AB - When allylamine is used as the amino input in Ugi-Smiles couplings of o-nitrophenols, the resulting adducts can be deallylated by a palladiumcatalyzed process leading to a formal Ugi-Smiles coupling with ammonia. This new sequence, combined with hydrogenolysis of the nitro group, offers an interesting multicomponent entry to benzotriazole and benzimidazole scaffolds.

UR - https://www.scopus.com/pages/publications/62749109142

U2 - 10.1021/ol8029438

DO - 10.1021/ol8029438

M3 - Article

C2 - 19170618

AN - SCOPUS:62749109142

SN - 1523-7060

VL - 11

SP - 995

EP - 997

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides

Abstract

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