The Mannich reaction in the synthesis of N,S-containing heterocycles. 7. Effective one-pot synthesis of derivatives of spiro[3,5,7,11-tetraazatricyclo-[7.3.1.02,7]tridec-2-ene-13,4′-piperidine] |
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Authors: | V. V. Dotsenko S. G. Krivokolysko V. P. Litvinov |
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Affiliation: | (1) “ChemEx” Laboratory, Vladimir Dal East-Ukrainian National University, Lugansk, 91034, Ukraine;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913 |
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Abstract: | 5,11-Disubstituted derivatives of 1′-isopropyl-8-thioxospiro[3,5,7,11-tetrazatricyclo[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]-1,9-dicar bonitrile was obtained by the interaction of 10-amino-9-aza-3-azonia-7,11-dicyano-3-isopropylspiro[5,5]undeca-7,10-diene-8-thiolate with 2 equiv. of a primary amine and excess of formaldehyde. An anomalous reaction product was obtained with o-toluidine — 7,9-dicyano-1′-isopropyl-3-(2-methylphenyl)-1,2,3,4-tetrahydrospiro[pyrido[1,2-a][1,3,5]triazine-8,4′-piper idinium]-6-thiolate. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, 1709–1713, November, 2007. |
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Keywords: | 10-amino-9-aza-3-azonia-7,11-dicyano-3-isopropylspiro[5,5]undeca-7,1-diene-8-thiolate pyridine-2-thiolates spiro[3,5,7,11]-tetraazatricyclo[7.3.1.02,7]tridec-2-ene-13,4′ -piperidine]-1,9-dicarbonitrile aminomethylation the Mannich reaction cyclocondensation |
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