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3-Formylchromones IV. The Rearrangement of 3-Formylchromone Enamines as a Simple, Facile Route to Novel Pyrazolo[3,4-b]pyridines and the Synthetic Utility of the Latter
Molecules 2005, 10(7), 822-832; doi:10.3390/10070822
Article

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

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Received: 8 March 2005 / Accepted: 12 April 2005 / Published: 31 August 2005
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Abstract

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.
Keywords: Tetrahalo-1; 4-benzoquinones; Cyclocondensation; Heterocyclic compounds. Tetrahalo-1; 4-benzoquinones; Cyclocondensation; Heterocyclic compounds.
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Hassan, A.; Mourad, A.; El-Shaieb, K.; Abou-Zied, A. Synthesis of 1,3,4-Thiadiazole, 1,3,4-Thiadiazine, 1,3,6-Thiadiazepane and Quinoxaline Derivatives from Symmetrical Dithiobiureas and Thioureidoethylthiourea Derivatives. Molecules 2005, 10, 822-832.

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