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 heterocycle 2a was confirmed by single-crystal X-ray analysis and its mechanism of formation supported by DFT computations.
Metadaten
Author:Debabrata Samanta, Anup Rana, Jan W. Bats, Michael Schmittel
URN:urn:nbn:de:hebis:30:3-373620
DOI:https://doi.org/10.3762/bjoc.10.317
ISSN:1860-5397
Pubmed Id:https://pubmed.ncbi.nlm.nih.gov/25670969
Parent Title (English):Beilstein journal of organic chemistry
Publisher:Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Place of publication:Frankfurt, Main
Contributor(s):D. O'Hagan
Document Type:Article
Language:English
Year of Completion:2014
Date of first Publication:2014/12/15
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2015/04/25
Tag:1,2,4-thiadiazoles; DFT; carbodiimide; cyclization; dithiourea
Volume:10
Page Number:8
First Page:2989
Last Page:2996
Note:
Copyright © 2014, Samanta et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://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: (http://www.beilstein-journals.org/bjoc)
HeBIS-PPN:369146077
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Sammlungen:Universitätspublikationen
Licence (German):License LogoCreative Commons - Namensnennung 2.0

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