The Mannich reaction in the synthesis of N,S-containing heterocycles |
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| Authors: | V V Dotsenko S G Krivokolysko E B Rusanov V P Litvinov |
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| Institution: | (1) ChemEx Laboratory, V. Dal’ East-Ukrainian National University, 20a Molodyozhny kv., 91034 Lugansk, Ukraine;(2) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 ul. Murmanskaya, 02094 Kiev, Ukraine;(3) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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| Abstract: | Reactions of 6-aryl-5-cyano-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidines with formaldehyde and primary amines gave earlier
unknown 3,4-dihydro-2H,6H-pyrimido2,1-b]-1,3,5]thiadiazine derivatives in 58–94% yields. In boiling AcOH, these pyrimidothiadiazines underwent the retro-Mannich
reaction leading to the starting pyrimidine-2-thiones. The structure of 3-(4-ethoxyphenyl)-6-oxo-8-phenyl-3,4-dihydro-2H,6H-pyrimido2,1-b]1,3,5]thiadiazine-7-carbonitrile was studied by X-ray diffraction analysis.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1384–1387, July, 2007. |
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| Keywords: | the Mannich reaction 6-aryl-5-cyano-4-oxo-2-thioxo-1 2 3 4-tetrahydropyrimidines formaldehyde primary amines pyrimido[2 1-b][1 3 5]thiadiazines the retro-Mannich reaction X-ray diffraction analysis |
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