Thiols in Ugi- and passerini-smiles-type couplings

Anaëlle Barthelon; Laurent El Kaïm; Marie Gizolme; Laurence Grimaud

doi:10.1002/ejoc.200800859

Thiols in Ugi- and passerini-smiles-type couplings

Anaëlle Barthelon
, Laurent El Kaïm
, Marie Gizolme
, Laurence Grimaud

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

Abstract

The use of the Smiles rearrangement in Ugi-type couplings with aromatic mercaptans allows for the straightforward, multicomponent formation of α-arylamino thiocarboxamides. The scope of this new four-component coupling is further broadened with the use of heterocyclic mercapto derivatives that afford thioamides of high biological interest in one step.

Original language	English
Pages (from-to)	5974-5987
Number of pages	14
Journal	European Journal of Organic Chemistry
Issue number	35
DOIs	https://doi.org/10.1002/ejoc.200800859
Publication status	Published - 1 Dec 2008

Keywords

Isocyanides
Multicomponent reactions
Rearrangement
Smiles reaction
Thiols
Ugi reaction

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10.1002/ejoc.200800859

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title = "Thiols in Ugi- and passerini-smiles-type couplings",

abstract = "The use of the Smiles rearrangement in Ugi-type couplings with aromatic mercaptans allows for the straightforward, multicomponent formation of α-arylamino thiocarboxamides. The scope of this new four-component coupling is further broadened with the use of heterocyclic mercapto derivatives that afford thioamides of high biological interest in one step.",

keywords = "Isocyanides, Multicomponent reactions, Rearrangement, Smiles reaction, Thiols, Ugi reaction",

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year = "2008",

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doi = "10.1002/ejoc.200800859",

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AU - Barthelon, Anaëlle

AU - El Kaïm, Laurent

AU - Gizolme, Marie

AU - Grimaud, Laurence

PY - 2008/12/1

Y1 - 2008/12/1

N2 - The use of the Smiles rearrangement in Ugi-type couplings with aromatic mercaptans allows for the straightforward, multicomponent formation of α-arylamino thiocarboxamides. The scope of this new four-component coupling is further broadened with the use of heterocyclic mercapto derivatives that afford thioamides of high biological interest in one step.

AB - The use of the Smiles rearrangement in Ugi-type couplings with aromatic mercaptans allows for the straightforward, multicomponent formation of α-arylamino thiocarboxamides. The scope of this new four-component coupling is further broadened with the use of heterocyclic mercapto derivatives that afford thioamides of high biological interest in one step.

KW - Isocyanides

KW - Multicomponent reactions

KW - Rearrangement

KW - Smiles reaction

KW - Thiols

KW - Ugi reaction

U2 - 10.1002/ejoc.200800859

DO - 10.1002/ejoc.200800859

M3 - Article

AN - SCOPUS:56749146248

SN - 1434-193X

SP - 5974

EP - 5987

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

Thiols in Ugi- and passerini-smiles-type couplings

Abstract

Keywords

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