A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives

A versatile synthetic procedure is described to prepare the benzimidazole-fused 1,2,4-thiadiazoles 2a–c via a methanesulfonyl chloride initiated multistep cyclization involving the intramolecular reaction of an in-situ generated carbodiimide with a thiourea unit. The structure of the intricate heter...

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Detalles Bibliográficos
Autores principales: Samanta, Debabrata, Rana, Anup, Bats, Jan W, Schmittel, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311674/
https://www.ncbi.nlm.nih.gov/pubmed/25670969
http://dx.doi.org/10.3762/bjoc.10.317
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author Samanta, Debabrata
Rana, Anup
Bats, Jan W
Schmittel, Michael
author_facet Samanta, Debabrata
Rana, Anup
Bats, Jan W
Schmittel, Michael
author_sort Samanta, Debabrata
collection PubMed
description A versatile synthetic procedure is described to prepare the benzimidazole-fused 1,2,4-thiadiazoles 2a–c via a methanesulfonyl chloride initiated multistep cyclization involving the intramolecular reaction of an in-situ generated carbodiimide with a thiourea unit. The structure of the intricate heterocycle 2a was confirmed by single-crystal X-ray analysis and its mechanism of formation supported by DFT computations.
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spelling pubmed-43116742015-02-10 A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives Samanta, Debabrata Rana, Anup Bats, Jan W Schmittel, Michael Beilstein J Org Chem Full Research Paper A versatile synthetic procedure is described to prepare the benzimidazole-fused 1,2,4-thiadiazoles 2a–c via a methanesulfonyl chloride initiated multistep cyclization involving the intramolecular reaction of an in-situ generated carbodiimide with a thiourea unit. The structure of the intricate heterocycle 2a was confirmed by single-crystal X-ray analysis and its mechanism of formation supported by DFT computations. Beilstein-Institut 2014-12-15 /pmc/articles/PMC4311674/ /pubmed/25670969 http://dx.doi.org/10.3762/bjoc.10.317 Text en Copyright © 2014, Samanta et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Samanta, Debabrata
Rana, Anup
Bats, Jan W
Schmittel, Michael
A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
title A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
title_full A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
title_fullStr A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
title_full_unstemmed A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
title_short A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
title_sort one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311674/
https://www.ncbi.nlm.nih.gov/pubmed/25670969
http://dx.doi.org/10.3762/bjoc.10.317
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