1401070-25-4Relevant academic research and scientific papers
Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates
Dotsenko, Victor V.,Frolov, Konstantin А.,Krivokolysko, Sergey G.,Chigorina, Elena A.,Pekhtereva, Tatyana M.,Suykov, Sergey Yu.,Papayanina, Elena S.,Dmitrienko, Artem О.,Bushmarinov, Ivan S.
, p. 116 - 127 (2016)
[Figure not available: see fulltext.]The structure of reaction products obtained from 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates, primary amines, and formaldehyde substantially depends on the nature of counter-ion (morpholinium or N-methylmorpholinium), as well as on the primary amine structure and the ratio of reactants. Aminomethylation of these thiolates with highly nucleophilic amines RCH2NH2 and excess formalin (2 equiv and more) produced 7-RCH2-9,9-dimethyl-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitrile salts, which gave the respective bispidines upon acidification. Performing this reaction with aromatic amines in the case of N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate led to analogous bispidines, while the morpholinium salt gave 3-aryl-8,8-dimethyl-7-[(morpholin-4-yl)methyl]-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-7,9-dicarbonitriles. The treatment of thiolates with 1 equiv of НСНО and 1 equiv of RCH2NH2 led to 7-RCH2-4-amino-9,9-dimethyl-2-oxo-6-thioxo-3,7-diazabicyclo[3.3.1]non-3-ene-1-carbonitriles. The molecular and crystal structures of key compounds were studied in detail by X-ray structural analysis.
