Synthesis, crystal structure, and interconversions of new N aryl 1,3,5 dithiazinanes, 1,3,5 thiadiazinanes, and 1,5 dithia 3,7 diazacyclooctanesChemoselectivity of multicomponent reaction of anilines with the CH 2 O-H 2 S thiomethyl ating mixture in the synthesis of N aryl substituted 1,3,5 dithiazinanes, 1,3,5 thiadiazinanes, and 1,5 dithia 3,7 diazacyclooctanes has been studied depending on the type and mutual arrangement of substituents in the starting anilines, ratio of reagents, temperature, and reac tion time. Conformation of the synthesized heterocycles in crystal has been found by X ray diffraction. Interconversion of the heterocycles showed stability of N aryl 1,3,5 dithiazinanes.
Other 6-membered heterocycles R 0670Cyclothiomethylation of Functional Substituted Anilines by CH2O and H2S. -Cyclocondensation of aminobenzoic acid derivatives (I), (V), (VII) and aniline sulfamide (XI) with formalin (II) and in situ prepared hydrogen sulfide under optimized conditions leads to formation of the corresponding dithiazinanes, while derivatives (Ia) and (VII) additionally afford thiazetidines (IVa) and (IX), respectively. The regioselective synthesis of thiadiazinane (X) is carried out at 0°C. Heterocycle (X) can be completely converted into dithiazinane (VIII) using a three-molar excess of the thiomethylation mixture. In the reaction of sulfamide (XI) at higher temperature, condensation leads to cyclodimer (XIII). The analogous cyclocondensation of aniline sulfacetamid (XV) only proceeds under acidic conditions to give the cyclodimer (XVI). The reaction to bisdithiazinanes (XIV) is more effective in acid medium. -(AKHMETOVA*, V. R.; NADYRGULOVA, G. R.; NIATSHINA, Z. T.; KHAIRULLINA, R. R.; STARIKOVA, Z. A.; BORISOVA, A. O.; ANTIPIN, M. Y.; KUNAKOVA, R. V.; DZHEMILEV, U. M.; Heterocycles 78 (2009) 1, 45-57; Inst. Petrochem. Catal., Bashkortostan Rep. Acad. Sci., Ufa 450075, Russia; Eng.) -H. Hoennerscheid 23-170
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