Journal Article10.1134/S1070428008020036
Multicomponent heterocyclization of carboxamides with H2S and CH2O
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TL;DR: In this article, multicomponent heterocyclization of aliphatic amides with H2S and CH2O (1:3:2) in water-organic solvent mixture in the presence of BuONa led to the formation of 1,3,5-dithiazinane in high yield (30-95%) and with high selectivity (100%).
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Abstract: Multicomponent heterocyclization of aliphatic amides with H2S and CH2O (1:3:2) in water-organic solvent mixture in the presence of BuONa led to the formation of 1,3,5-dithiazinane in high yield (30–95%) and with high selectivity (100%). Under these conditions benzamide gave 3,5-dibenzoyl-1,3,5-thiadiazinane in 74% yield, whereas due to ortho-effect the acetylsalicylamide with H2S and CH2O in a system BuOH-H2O without BuONa formed N-acetylsalicyloyl-1,3,5-dithiazinane (80%). Heterocyclization of α-aminosuccinic acid monoamide depending on the H2S and CH2O concentration occurred either at one or both NH2 yielding respectively mono-or bisdithiazinanes.
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Citations
Disulfide- and multisulfide-containing metabolites from marine organisms.
TL;DR: Disulfideand Multisulfide-Containing Metabolites from Marine Organisms and their Applications in Physiological Chemistry and Drug Research.
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Multicomponent reactions of amines with aldehydes and H2S as efficient route to heterocycles and thioaza macrocycles
Vnira R. Akhmetova,G. R. Khabibullina,E. B. Rakhimova,R. A. Vagapov,R. R. Khairullina,Z. T. Niatshina,N. N. Murzakova +6 more
TL;DR: New experimental results on multicomponent reactions of amines with aldehydes and H2S in the directed synthesis of functionally-substituted 1,3-thiazetidines,1,3,5-dithiazinanes, 1,4-thia-3,7-diazacyclooctanes, and thioaza macrocycles are provided.
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One-pot cyclothiomethylation of amines as efficient method for the synthesis of saturated five-, six-, seven-, and eight-membered S,N-Heterocycles
TL;DR: In this paper, a review generalizes and systemizes published data on the synthesis of biologically active saturated five-, six-, seven-, and eight-membered S,N-heterocycles, focusing on cyclothiomethylation of various amines by two-component systems CH2O-H2S (or thiols) and RCHO-CS2 (or S2Cl2).
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Efficient catalytic method for the synthesis of N -aryl-substituted 1,5,3-dithiazamacroheterocycles
N. N. Makhmudiyarova,L. V. Mudarisova,E. S. Meshcheryakova,Askhat G. Ibragimov,Usein M. Dzhemilev +4 more
TL;DR: In this paper, a cycloaminomethylation of α,ω-dithiols (butane-1,4-, pentane- 1,5-, hexane- 2,6-dichiols and 3, 6-dioxaoctane)-1,8-didiols using N, N -bis(methoxymethyl)- N -arylamines and Sm- and Cu-containing catalysts is reported.
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One-pot synthesis of bis-1,5,3-dithiazepanes from ethane-1,2-dithiol, formaldehyde, and ammonium salts
TL;DR: In this paper, an efficient one-pot procedure for the synthesis of bis-1,5,3-dithiazepanes by reaction of ethane-1 2 dithiol with formaldehyde and ammonium salts was developed.
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References
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