Synthesis of thiadiazole, dithietane, and imine derivatives of the [1,2]dithiolo[1,4]thiazine ring system

被引:18
作者
Barriga, S
Fuertes, P
Marcos, CF
Miguel, D
Rakitin, OA
Rees, CW
Torroba, T [1 ]
机构
[1] Univ Burgos, Fac Ciencias, Dept Quim, Burgos 09001, Spain
[2] Univ Extremadura, Fac Vet, Dept Quim Organ, Caceres 10071, Spain
[3] Univ Valladolid, Fac Ciencias, Dept Quim Inorgan, E-47005 Valladolid, Spain
[4] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 117913, Russia
[5] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England
关键词
D O I
10.1021/jo010368u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the synthesis of some new polysulfur-nitrogen heterocyclics by cycloaddition reactions to the thioketo group of readily available tricyclic 1,2-dithiole-3-thiones. Thus treatment of bis-[1,2]dithiolo[1,4]thiazine ketothione 1 with diaryl nitrile imines generated from hydrazonoyl chlorides 2a-g gave [1,3,4]thiadiazolylidenyl[1,2]dithiolo[1,4]thiazines 4a-g in high yield. Compounds 4a-f, bearing the same substituents in both aryl groups, were stable but the analogous 4g,h with a p-nitrophenyl group on carbon gave the bis[1,2]dithiolo[1,4]thiazine dione 9, probably by cycloreversion and hydrolysis during chromatography. Treatment of 1, the bis [1,2] dithiolopyrrole ketothione 13, and dithione 12 with ethoxycarbonyl azide 11 gave imines 12 and 15 and bisimine 16, respectively, by an alternative fragmentation of the initial cycloadduct in which the 1,2-dithiole ring is retained. Reaction of 1 with TosMIC gave the imino-1,3-dithietane 17.
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页码:5766 / 5771
页数:6
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