311333-67-2Relevant academic research and scientific papers
The mannich reaction in the synthesis of N,S-containing heterocycles 4. Aminomethylation of 6-amino-3,5-dicyano-1,4-dihydropyridine-2-thiolates: A convenient regioselective route to 3,5,7,11-tetraazatricyclo[7.3.1.0 2,7]tridec-2-ene derivatives
Dotsenko,Krivokolysko,Chernega,Litvinov
, p. 1053 - 1062 (2007)
Treatment of N-methylmorpholinium 4-R-6-amino-3,5-dicyano-1,4- dihydropyridine-2-thiolates (R = 2-ClC6H4 and 2-MeOC 6H4) with primary amines in the presence of an excess of formaldehyde gave 13-R-8-thioxo-3,5,7,11-tetraazatricyclo[7.3.1.0 2,7]tridec-2-ene-1,9-dicarbonitrile derivatives in high yields (66-95%). In a similar way, aminomethylation of 3-R-10-amino-7,11-dicyano-9-aza- 3-azoniaspiro[5.5]undeca-7,10-diene-8-thiolates (R = Me and Et) afforded 1'-alkyl-8-thioxospiro[3,5,7,11-tetraazatricyclo[7.3.1.02,7]tridec-2- ene-13,4'-piperidine]-1,9-dicarbonitriles in 43-91% yields. Alternatively, these compounds were obtained by multicomponent cyclocondensation of N-alkylpiperidin-4-ones, cyanothioacetamide, primary amines, and aqueous formaldehyde. The starting 3-R-10-amino-7,11-dicyano-9-aza-3-azoniaspiro[5.5] undeca-7,10-diene-8-thiolates were prepared by a new method from N-alkylpiperidin-4-ones and cyanothioacetamide. The structure of 5,11-bis(4-ethoxyphenyl)-13-(2-methoxyphenyl)-8-thioxo-3,5,7, 11-tetraazatricyclo[7.3.1.02,7]tridec-2-ene-1,9-dicarbonitrile was examined by X-ray diffraction analysis.
One-step synthesis of substituted 3,5-dicyanospiro-4-(piperidine-4′)- 1H,4H-dihydropyridine-2-thiolates and 2,6-diamino-3,5-dicyanospiro-4- [(piperidine-4′) or (2′-oxoindole-3′)]-4H-thiopyrans
Shestopalov, Anatoliy M.,Shestopalov, Alexander A.,Rodinovskaya, Lyudmila A.,Gromova, Anna V.
experimental part, p. 1100 - 1114 (2010/02/28)
A new, one-step method for the synthesis of substituted 3,5-dicyanospiro-4(piperidine-4′)-1H,4H-dihydropyridine-3-thiolates and 2,6-diamino-3,5-dicyanospiro-4-[(piperidine-4′) or (2′ -oxoindole-3′)]-4H-thiopyrans using a multicomponent reaction of N-substituted piperidine-4-ones and isatins with derivatives of cyanoacetic acid is described. The regioselectivity of this reaction can be controlled by varying the substituents at the nitrogen atom of the piperidine-4-ones. The multicomponent reaction of N-alkylpiperidine-4-ones with malononitrile and cyanothioacetamide gives spiro-4-(1′ -alkylpiperidine-4′)-1H,4H- dihydropyridine-2-thiolates, whereas a similar reaction of N-(acyl) alkoxycarbonylpiperidine-4-ones leads exclusively to spiro-4-(1′ -(acyl)alkoxycarbonylpiperidine-4′)-4H-thiopyrans. Taylor & Francis Group, LLC.
