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

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 fr...

Descripción completa

Detalles Bibliográficos
Autores principales: Kruithof, Art, Vande Velde, Christophe M. L., Ruijter, Eelco, Orru, Romano V. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154663/
https://www.ncbi.nlm.nih.gov/pubmed/28350361
http://dx.doi.org/10.3390/molecules22040541
_version_ 1783357736125202432
author Kruithof, Art
Vande Velde, Christophe M. L.
Ruijter, Eelco
Orru, Romano V. A.
author_facet Kruithof, Art
Vande Velde, Christophe M. L.
Ruijter, Eelco
Orru, Romano V. A.
author_sort Kruithof, Art
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6154663
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61546632018-11-13 Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions Kruithof, Art Vande Velde, Christophe M. L. Ruijter, Eelco Orru, Romano V. A. Molecules Article 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. MDPI 2017-03-28 /pmc/articles/PMC6154663/ /pubmed/28350361 http://dx.doi.org/10.3390/molecules22040541 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kruithof, Art
Vande Velde, Christophe M. L.
Ruijter, Eelco
Orru, Romano V. A.
Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions
title Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions
title_full Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions
title_fullStr Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions
title_full_unstemmed Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions
title_short Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions
title_sort thiazine-2-thiones as masked 1-azadienes in cascade dimerization reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154663/
https://www.ncbi.nlm.nih.gov/pubmed/28350361
http://dx.doi.org/10.3390/molecules22040541
work_keys_str_mv AT kruithofart thiazine2thionesasmasked1azadienesincascadedimerizationreactions
AT vandeveldechristopheml thiazine2thionesasmasked1azadienesincascadedimerizationreactions
AT ruijtereelco thiazine2thionesasmasked1azadienesincascadedimerizationreactions
AT orruromanova thiazine2thionesasmasked1azadienesincascadedimerizationreactions

Ejemplares similares