Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives

Reactions of N,N′-disubstituted hydrazinecarbothioamides 8a-c and substituted thioureidoethylthioureas 9a-c with 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil, 10a) and 2,3,5,6-tetrabromo-1,4-benzoquinone (bromanil, 10b) to form N,N′-disubstituted [1,3,4]thiadiazole-2,5-diamines 11a-c, 6,7-dichlor...

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Autores principales: Hassan, Alaa A., Mourad, Aboul-Fetouh E., El-Shaieb, Kamal M., Abou-Zied, Ashraf H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2005
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147614/
https://www.ncbi.nlm.nih.gov/pubmed/18007352
http://dx.doi.org/10.3390/10070822
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author Hassan, Alaa A.
Mourad, Aboul-Fetouh E.
El-Shaieb, Kamal M.
Abou-Zied, Ashraf H.
author_facet Hassan, Alaa A.
Mourad, Aboul-Fetouh E.
El-Shaieb, Kamal M.
Abou-Zied, Ashraf H.
author_sort Hassan, Alaa A.
collection PubMed
description Reactions of N,N′-disubstituted hydrazinecarbothioamides 8a-c and substituted thioureidoethylthioureas 9a-c with 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil, 10a) and 2,3,5,6-tetrabromo-1,4-benzoquinone (bromanil, 10b) to form N,N′-disubstituted [1,3,4]thiadiazole-2,5-diamines 11a-c, 6,7-dichloro-3-substituted amino-1H-benzo[1,3,4]-thiadiazine-5,8-diones 12a-c, 2,3,7,8-tetrahalothianthrene-1,4,6,9-tetraones 13a,b, 5,6,8-trihalo-7-oxo-3,7-dihydro-2H-quinoxaline-1-carbothioic acid substituted amides 14a-c, 15a-c and 7-substituted imino-[1,3,6]thiadiazepane-3-thiones 16a-c are reported. Rationales for the observed conversions are presented.
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spelling pubmed-61476142018-11-19 Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives Hassan, Alaa A. Mourad, Aboul-Fetouh E. El-Shaieb, Kamal M. Abou-Zied, Ashraf H. Molecules Article Reactions of N,N′-disubstituted hydrazinecarbothioamides 8a-c and substituted thioureidoethylthioureas 9a-c with 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil, 10a) and 2,3,5,6-tetrabromo-1,4-benzoquinone (bromanil, 10b) to form N,N′-disubstituted [1,3,4]thiadiazole-2,5-diamines 11a-c, 6,7-dichloro-3-substituted amino-1H-benzo[1,3,4]-thiadiazine-5,8-diones 12a-c, 2,3,7,8-tetrahalothianthrene-1,4,6,9-tetraones 13a,b, 5,6,8-trihalo-7-oxo-3,7-dihydro-2H-quinoxaline-1-carbothioic acid substituted amides 14a-c, 15a-c and 7-substituted imino-[1,3,6]thiadiazepane-3-thiones 16a-c are reported. Rationales for the observed conversions are presented. MDPI 2005-08-31 /pmc/articles/PMC6147614/ /pubmed/18007352 http://dx.doi.org/10.3390/10070822 Text en © 2005 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Hassan, Alaa A.
Mourad, Aboul-Fetouh E.
El-Shaieb, Kamal M.
Abou-Zied, Ashraf H.
Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives
title Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives
title_full Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives
title_fullStr Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives
title_full_unstemmed Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives
title_short Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thia-diazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives
title_sort synthesis of 1,3,4-thiadiazole, 1,3,4-thiadiazine, 1,3,6-thia-diazepane and quinoxaline derivatives from symmetrical dithiobiureas and thioureidoethylthiourea derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147614/
https://www.ncbi.nlm.nih.gov/pubmed/18007352
http://dx.doi.org/10.3390/10070822
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