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Molecules 2017, 22(4), 541; doi:10.3390/molecules22040541

Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions)

1
Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081HZ Amsterdam, The Netherlands
2
Faculty of Applied Engineering, Advanced eactor Technology, University of Antwerp, Groenenborgerlaan 171, 2018 Antwerpen, Belgium
*
Author to whom correspondence should be addressed.
Received: 28 February 2017 / Revised: 24 March 2017 / Accepted: 26 March 2017 / Published: 28 March 2017
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
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Abstract

We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as “masked” 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity. View Full-Text
Keywords: 1-azadienes; multicomponent reaction; thiazine-2-thiones; tetrahydropyrimidines; aza-Diels-Alder; chemical space; molecular diversity; microwave 1-azadienes; multicomponent reaction; thiazine-2-thiones; tetrahydropyrimidines; aza-Diels-Alder; chemical space; molecular diversity; microwave
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kruithof, A.; Vande Velde, C.M.L.; Ruijter, E.; Orru, R.V.A. Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions). Molecules 2017, 22, 541.

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