Synthesis of 1,3,4-thiadiazole, 1,3,4-thiadiazine, 1,3,6-thiadiazepane 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-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.
Hassan
Alaa A
AA
Chemistry Department, Faculty of Science, El-Minia University, A. R. Egypt. alaahassan2001@yahoo.com
Mourad
Aboul-Fetouh
AF
El-Shaieb
Kamal M
KM
Abou-Zied
Ashraf H
AH
D004220:Disulfides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D011810:Quinoxalines / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013829:Thiadiazines / Q000138:chemical synthesis*; D013830:Thiadiazoles / Q000138:chemical synthesis*; D013844:Thiazoles / Q000737:chemistry; D013853:Thioacetamide / Q000737:chemistry; D013890:Thiourea / Q000031:analogs & derivatives* / Q000737:chemistry*; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry
D004220:Disulfides; D006571:Heterocyclic Compounds; D011810:Quinoxalines; D013438:Sulfhydryl Compounds; D013829:Thiadiazines; D013830:Thiadiazoles; D013844:Thiazoles; D013853:Thioacetamide; D014050:Toluene; D013890:Thiourea; C004848:dithiol