Thiazole formation through a modified Gewald reaction

The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the su...

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Main Authors: Carl J. Mallia, Lukas Englert, Gary C. Walter, Ian R. Baxendale
Format: Article
Language:English
Published: Beilstein-Institut 2015-05-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.11.98
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author Carl J. Mallia
Lukas Englert
Gary C. Walter
Ian R. Baxendale
author_facet Carl J. Mallia
Lukas Englert
Gary C. Walter
Ian R. Baxendale
author_sort Carl J. Mallia
collection DOAJ
description The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.
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spelling doaj.art-46dd88a9713741989f98b62ba1dc36742022-12-21T23:04:44ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-05-0111187588310.3762/bjoc.11.981860-5397-11-98Thiazole formation through a modified Gewald reactionCarl J. Mallia0Lukas Englert1Gary C. Walter2Ian R. Baxendale3Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United KingdomDepartment of Chemistry, Durham University, South Road, Durham, DH1 3LE, United KingdomSyngenta CP R&D Chemistry, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United KingdomDepartment of Chemistry, Durham University, South Road, Durham, DH1 3LE, United KingdomThe synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.https://doi.org/10.3762/bjoc.11.98design of experiment (DOE)1,4-dithiane-2,5-diolGewald reactionthiazolethiophene
spellingShingle Carl J. Mallia
Lukas Englert
Gary C. Walter
Ian R. Baxendale
Thiazole formation through a modified Gewald reaction
Beilstein Journal of Organic Chemistry
design of experiment (DOE)
1,4-dithiane-2,5-diol
Gewald reaction
thiazole
thiophene
title Thiazole formation through a modified Gewald reaction
title_full Thiazole formation through a modified Gewald reaction
title_fullStr Thiazole formation through a modified Gewald reaction
title_full_unstemmed Thiazole formation through a modified Gewald reaction
title_short Thiazole formation through a modified Gewald reaction
title_sort thiazole formation through a modified gewald reaction
topic design of experiment (DOE)
1,4-dithiane-2,5-diol
Gewald reaction
thiazole
thiophene
url https://doi.org/10.3762/bjoc.11.98
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AT garycwalter thiazoleformationthroughamodifiedgewaldreaction
AT ianrbaxendale thiazoleformationthroughamodifiedgewaldreaction