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DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones

Sebastian Antony Savarimuthu, Devarajan Gnanaprakasi Leo Prakash, Selvaraj Augustine Thomas, Thirumanavelan Gandhi, Leo Prakash Orcid Logo

ChemistrySelect, Volume: 3, Issue: 46, Pages: 13087 - 13090

Swansea University Author: Leo Prakash Orcid Logo

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DOI (Published version): 10.1002/slct.201802731

Abstract

5‐exo‐dig is a versatile Baldwin tool to predict and make useful heterocyclic compounds from nucleophiles and electrophiles. In order to aid this, a novel metal‐free method is proposed to produce [1,3]‐oxathiole‐2‐thiones from a readily synthesized propargyl alcohols and easily accessible carbon dis...

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Published in: ChemistrySelect
ISSN: 2365-6549 2365-6549
Published: 2018
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URI: https://cronfa.swan.ac.uk/Record/cronfa48077
first_indexed 2019-01-08T14:02:17Z
last_indexed 2019-02-25T19:53:43Z
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spelling 2019-02-25T16:53:46.6799473 v2 48077 2019-01-08 DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones bd72868c48af6c0b04bf9f6bb48ce324 0000-0002-8812-8927 Leo Prakash Leo Prakash true false 2019-01-08 EAAS 5‐exo‐dig is a versatile Baldwin tool to predict and make useful heterocyclic compounds from nucleophiles and electrophiles. In order to aid this, a novel metal‐free method is proposed to produce [1,3]‐oxathiole‐2‐thiones from a readily synthesized propargyl alcohols and easily accessible carbon disulfide, where both secondary and primary propargyl alcohols are compatible to this methodology. This procedure is simple, versatile, atom economy and functional group tolerance resulting in moderate to excellent yields. Finally, the process was screened on different mode of reaction operation. Journal Article ChemistrySelect 3 46 13087 13090 2365-6549 2365-6549 Carbon disulfide, Double bond rearrangement, 5-exo-dig, [1,3]-Oxathiole-2-thione, Propargyl alcohol 31 12 2018 2018-12-31 10.1002/slct.201802731 COLLEGE NANME Engineering and Applied Sciences School COLLEGE CODE EAAS Swansea University 2019-02-25T16:53:46.6799473 2019-01-08T10:54:52.0243290 Faculty of Science and Engineering School of Engineering and Applied Sciences - Materials Science and Engineering Sebastian Antony Savarimuthu 1 Devarajan Gnanaprakasi Leo Prakash 2 Selvaraj Augustine Thomas 3 Thirumanavelan Gandhi 4 Leo Prakash 0000-0002-8812-8927 5 0048077-14012019095141.pdf savarimuthu2018v2.pdf 2019-01-14T09:51:41.8530000 Output 588120 application/pdf Accepted Manuscript true 2019-12-07T00:00:00.0000000 true eng
title DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
spellingShingle DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
Leo Prakash
title_short DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
title_full DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
title_fullStr DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
title_full_unstemmed DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
title_sort DBU‐Mediated Intermolecular 5‐exo‐dig Cyclization of PropargylAlcohols and Carbon Disulfide to [1,3]‐Oxathiole‐2‐thiones
author_id_str_mv bd72868c48af6c0b04bf9f6bb48ce324
author_id_fullname_str_mv bd72868c48af6c0b04bf9f6bb48ce324_***_Leo Prakash
author Leo Prakash
author2 Sebastian Antony Savarimuthu
Devarajan Gnanaprakasi Leo Prakash
Selvaraj Augustine Thomas
Thirumanavelan Gandhi
Leo Prakash
format Journal article
container_title ChemistrySelect
container_volume 3
container_issue 46
container_start_page 13087
publishDate 2018
institution Swansea University
issn 2365-6549
2365-6549
doi_str_mv 10.1002/slct.201802731
college_str Faculty of Science and Engineering
hierarchytype
hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Materials Science and Engineering{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Materials Science and Engineering
document_store_str 1
active_str 0
description 5‐exo‐dig is a versatile Baldwin tool to predict and make useful heterocyclic compounds from nucleophiles and electrophiles. In order to aid this, a novel metal‐free method is proposed to produce [1,3]‐oxathiole‐2‐thiones from a readily synthesized propargyl alcohols and easily accessible carbon disulfide, where both secondary and primary propargyl alcohols are compatible to this methodology. This procedure is simple, versatile, atom economy and functional group tolerance resulting in moderate to excellent yields. Finally, the process was screened on different mode of reaction operation.
published_date 2018-12-31T04:29:40Z
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score 11.090464

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