Cyclothiomethylation of aryl hydrazines with formaldehyde and hydrogen sulfide |
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Authors: | V R Akhmetova G R Nadyrgulova T V Tyumkina Z A Starikova D G Golovanov M Yu Antipin R V Kunakova U M Dzhemilev |
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Institution: | (1) Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075 Ufa, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation;(3) Ufa State Academy of Economics and Service, 145 ul. Chernyshevskogo, 450077 Ufa, Russian Federation |
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Abstract: | Cyclothiomethylation of phenyl hydrazine with CH2O and H2S in a ratio of 1: 3: 2 in an acidic medium (HCl) afforded previously unknown 3-phenyl-1,3,4-thiadiazolidine (35% yield) and
N-phenyl(perhydro-1,3,5-dithiazin-5-yl)amine (35% yield). The analogous reaction in an alkaline medium (BuONa) produced N-phenyl(perhydro-1,3-thiazetidin-3-yl)amine (22% yield). The reaction of 1,2-diphenyl hydrazine with CH2O and H2S in an alkaline medium gave 1,2,4,5-tetraphenylhexahydro-1,2,4,5-tetrazine and previously unknown 3,4-diphenyl-1,3,4-thiadiazolidine
and 5,6-diphenyltetrahydro-1,3,5,6-dithiadiazepine in 39 and 22% yields, respectively. Cyclothiomethylation of benzyl hydrazine
afforded previously unknown bis(6-benzyl-4,2,6-thiadiazolidin-2-yl)methyl] sulfide (60% yield) and N-benzyl(perhydro-1,3,5-dithiazin-5-yl)amine (19% yield). The reaction of tosyl hydrazine produced 3-(p-tolyl)sulfonyl]-1,3,4-thiadiazolidine, N-(perhydro-1,3,5-dithiazin-5-yl)-p-tolylsulfonamide, and 3,7-bis(p-tolylsulfonylamino)-1,5-dithia-3,7-diazacyclooctane in 21, 38, and 41% yields, respectively.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1758–1767, October, 2006. |
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Keywords: | cyclothiomethylation aryl hydrazines formaldehyde hydrogen sulfide 1 3 5-dithiazines 1 3 4-thiadiazolidines X-ray diffraction study |
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