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Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles


Mloston, Grzegorz; Grzelak, Paulina; Mikina, Maciej; Linden, Anthony; Heimgartner, Heinz (2015). Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles. Beilstein Journal of Organic Chemistry, 11:576-582.

Abstract

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

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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:28 April 2015
Deposited On:30 Apr 2015 08:41
Last Modified:05 Apr 2016 19:14
Publisher:Beilstein-Institut
ISSN:1860-5397
Funders:National Science Center (Cracow, Poland) Grant Maestro-3 (Dec-2012/06/A/ST5/00219)
Free access at:Official URL. An embargo period may apply.
Publisher DOI:https://doi.org/10.3762/bjoc.11.63
Official URL:http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-11-63.pdf
Related URLs:http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-11-63
Permanent URL: https://doi.org/10.5167/uzh-110557

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