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First synthesis of ferrocenyl-substituted thiochalcones and their [4+2]-cycloadditions with acetylenic dienophiles


Mloston, Grzegorz; Hamera-Faldyga, Roza; Heimgartner, Heinz (2018). First synthesis of ferrocenyl-substituted thiochalcones and their [4+2]-cycloadditions with acetylenic dienophiles. Journal of Sulfur Chemistry, 39(3):322-331.

Abstract

Ferrocenyl methyl ketone reacts with aromatic aldehydes yielding 1-ferrocenyl-3-aryl-propenones (chalcones), which upon treatment with Lawesson’s reagent (LR) are converted to the corresponding thiochalcones. The latter enter the thia-Diels–Alder reaction with acetylenic dienophiles (DMAD and methyl propiolate) to give ferrocenyl-substituted 4H-thiopyrans. In the case of methyl propiolate, the formation of the six-membered ring occurs with complete regioselectivity.

Abstract

Ferrocenyl methyl ketone reacts with aromatic aldehydes yielding 1-ferrocenyl-3-aryl-propenones (chalcones), which upon treatment with Lawesson’s reagent (LR) are converted to the corresponding thiochalcones. The latter enter the thia-Diels–Alder reaction with acetylenic dienophiles (DMAD and methyl propiolate) to give ferrocenyl-substituted 4H-thiopyrans. In the case of methyl propiolate, the formation of the six-membered ring occurs with complete regioselectivity.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:January 2018
Deposited On:08 Feb 2018 10:32
Last Modified:27 May 2018 05:38
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:National Science Center (Cracow, Poland), Grant Maestro-3;Dec-2012/06/A/ST5/00219, Alexander von Humboldt Stiftung (Bonn, Germany)
Additional Information:This is an Accepted Manuscript of an article published by Taylor & Francis in Journal of Sulfur Chemistry on [2018], available online: http://wwww.tandfonline.com/10.1080/17415993.2018.1427749
OA Status:Green
Publisher DOI:https://doi.org/10.1080/17415993.2018.1427749
Project Information:
  • : FunderNational Science Center (Cracow, Poland)
  • : Grant ID
  • : Project TitleGrant Maestro-3;Dec-2012/06/A/ST5/00219
  • : FunderAlexander von Humboldt Stiftung (Bonn, Germany)
  • : Grant ID
  • : Project Title

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