A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride

A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride

The high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to the analogous transformations of the closely-relate...

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Bibliographic Details
Main Authors: Andreas S. Kalogirou, Panayiotis A. Koutentis
Format: Article
Language:English
Published: MDPI AG 2015-08-01
Series:Molecules
Subjects:
heterocycle
1,2,6-thiadiazines
Appel’s salt
1,2,3-dithiazoles
Online Access:http://www.mdpi.com/1420-3049/20/8/14576
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spelling doaj-c032dea04463431c996238a11f6e922c2020-11-24T22:46:32ZengMDPI AGMolecules1420-30492015-08-01208145761459410.3390/molecules200814576molecules200814576A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium ChlorideAndreas S. Kalogirou0Panayiotis A. Koutentis1Department of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, CyprusDepartment of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, CyprusThe high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to the analogous transformations of the closely-related 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt) into 4-chloro-5H-1,2,3-dithiazol-5-one and 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)malononitrile. Furthermore, cyclocondensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with 2-aminophenol and 1,2-benzenediamines gave fused 4H-1,2,6-thiadiazines in 68%–85% yields.http://www.mdpi.com/1420-3049/20/8/14576heterocycle1,2,6-thiadiazinesAppel’s salt1,2,3-dithiazoles
collection DOAJ
language English
format Article
sources DOAJ
author Andreas S. Kalogirou
Panayiotis A. Koutentis
spellingShingle Andreas S. Kalogirou
Panayiotis A. Koutentis
A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
Molecules
heterocycle
1,2,6-thiadiazines
Appel’s salt
1,2,3-dithiazoles
author_facet Andreas S. Kalogirou
Panayiotis A. Koutentis
author_sort Andreas S. Kalogirou
title A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
title_short A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
title_full A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
title_fullStr A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
title_full_unstemmed A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride
title_sort qualitative comparison of the reactivities of 3,4,4,5-tetrachloro-4h-1,2,6-thiadiazine and 4,5-dichloro-1,2,3-dithiazolium chloride
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2015-08-01
description The high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to the analogous transformations of the closely-related 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt) into 4-chloro-5H-1,2,3-dithiazol-5-one and 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)malononitrile. Furthermore, cyclocondensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with 2-aminophenol and 1,2-benzenediamines gave fused 4H-1,2,6-thiadiazines in 68%–85% yields.
topic heterocycle
1,2,6-thiadiazines
Appel’s salt
1,2,3-dithiazoles
url http://www.mdpi.com/1420-3049/20/8/14576
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