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Paper | Regular issue | Vol 78, No. 1, 2009, pp.45-57
Published online, 8th September, 2008
DOI: 10.3987/COM-08-11432
■ Cyclothiomethylation of Functional Substituted Anilines by CH2O and H2S

Vnira R. Akhmetova,* Guzel R. Nadyrgulova, Zalifa T. Niatshina, Regina R. Khairullina, Zoya A. Starikova, Alexandra O. Borisova, Michail Yu. Antipin, Raihana V. Kunakova, and Usein M. Dzhemilev

*Laboratory of Heteroatomic Compounds, Institute of Petrochemistry and Catalysis, RAS, 450075, Ufa, Prospekt Oktyabrya,141, Russia

Abstract

N-Aryl substituted 1,3,5-dithiazinanes have been synthesized (20-60 °C) in 32-95% yield by cyclocondensation of o-, p-aminobenzoic, 4-, 5-aminosalicylic acids, p-aminobenzoic acid ethyl or (β-diethylamino)ethyl esters and p-aniline sulfamide with CH2O and H2S (1:3:2 ratio). At ambient temperature p-aminobenzoic acid, 5-aminosalicylic acid and p-aminobenzoic acid ethyl ester together with 1,3,5-dithiazinanes form appropriate N-aryl substituted 1,3-thiazetidines. Cyclothiomethylation of p-aminobenzoic acid ethyl ester (0 °C) results in N,N-diaryl-1,3,5-thiadiazinane. Heterocyclization of p-aniline sulfamide with CH2O and H2S at a molar ratio of 1:6:4 (pH 1.3-1.5) was found to afford bis-1,3,5-dithiazinanes involving two amino groups. Condensation of p-aniline sulfacetamide with 37% formalin (CH2O) and H2S (pH 2.5) led to the compound, which was built as macroheterocycle from two fragments of p-aniline sulfacetamide molecule bound to each other by sym-dimethyl sulfide chain (CH2SCH2).