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Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles


Mloston, Grzegorz; Grzelak, Paulina; Heimgartner, Heinz (2017). Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles. Journal of Sulfur Chemistry, 38(1):1-10.

Abstract

Hetaryl-substituted thiochalcones react with acetylenic mono- and diesters in the THF solution in the presence of LiClO4 at 65°C to give, after 24h, 4H-thiopyran carboxylates and dicarboxylates, respectively, in moderate to good yields. The same reactions were performed also in the THF solution without a catalyst under microwave irradiation. In that case, the reaction time was reduced to three minutes and, in most cases, an improvement in the yield of the [4+2]-cycloadduct was observed. The reactions with methyl propiolate occurred regioselectively and the 3-carboxylates were formed exclusively.

Abstract

Hetaryl-substituted thiochalcones react with acetylenic mono- and diesters in the THF solution in the presence of LiClO4 at 65°C to give, after 24h, 4H-thiopyran carboxylates and dicarboxylates, respectively, in moderate to good yields. The same reactions were performed also in the THF solution without a catalyst under microwave irradiation. In that case, the reaction time was reduced to three minutes and, in most cases, an improvement in the yield of the [4+2]-cycloadduct was observed. The reactions with methyl propiolate occurred regioselectively and the 3-carboxylates were formed exclusively.

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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:2017
Deposited On:29 Sep 2016 12:07
Last Modified:18 Apr 2018 11:47
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:National Science Center (Cracow, Poland), Maestro (Dec-2012/06/A/ST5/00219)
OA Status:Green
Publisher DOI:https://doi.org/10.1080/17415993.2016.1230857

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