Aminomethylation of morpholinium and N-methylmorpholinium 3,5-dicyano-4,4-dimethyl-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates View Full Text


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Article Info

DATE

2016-02

AUTHORS

Victor V. Dotsenko, Konstantin А. Frolov, Sergey G. Krivokolysko, Elena A. Chigorina, Tatyana M. Pekhtereva, Sergey Yu. Suykov, Elena S. Papayanina, Artem О. Dmitrienko, Ivan S. Bushmarinov

ABSTRACT

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. More... »

PAGES

116-127

References to SciGraph publications

  • 2012-10. Synthesis of pyrido[2,1-b][1,3,5]thiadiazines by the aminomethylation of 4-methyl-6-oxo-2-thioxopiperidine-3-carbonitrile in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2008-06. An efficient Mannich-type synthesis of bis(pyrido[2,1-b][1,3,5]thiadiazin-7-yl)-methanes in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
  • 2012-05. On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2003-04. Synthesis and Structure of Pyrido[2,1-b][1,3,5]thiadiazine Derivatives in DOKLADY CHEMISTRY
  • 2015-02. Synthesis of partially hydrogenated 1,3,5-thiadiazines by Mannich reaction in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2007-03. Simple one-pot synthesis of 3,5,7,11-tetraazatricyclo[7.3.1.02,7]tridec-2-ene derivatives under Mannich reaction conditions in DOKLADY CHEMISTRY
  • 1997-07. Ethylcrotonates in synthesis of 4,4-disubstituted 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2010-12. Synthesis of derivatives of 3,5,7,11-tetraaza-tricyclo[7.3.1.02,7]tridec-2-ene-8-selenone in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2007-05. A Double Mannich-type Reaction in the 1,4,5,6-Tetrahydropyridine-2-thiolate Series: A Convenient Approach to Functionalized 3,7-Diazabicyclo[3.3.1]nonane Derivatives in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
  • 2008-03. The Synthesis of Cyclopenta[c]pyridine (2-Pyrindene) Derivatives in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
  • 2012-08. Synthesis of new heterocyclic system, pyrido[3,2-e][1,3]thiazine by mannich reaction in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2005-11. Aminomethylation of 1,2,3,4-Tetrahydropyridine-6-thiolates: A Novel Approach to Synthesis of 3,7-Diazabicyclo[3.3.1]nonane Derivatives in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2013-06. Synthesis and aminomethylation of 9-aza-3-azoniaspiro[5,5]undeca-7,10-diene-8-selenolates in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2007-01. An Efficient Mannich-Type One-Pot Synthesis of 3,5,7,11-Tetraazatricyclo [7.3.1.02,7]tridec-2-ene Derivatives Starting from Functionalized 1,4-Dihydropyridines in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
  • 2007-11. 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] in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 1983. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen in NONE
  • 2013-02. The First Example of 3,7-Diazabicyclo[3.3.1]nonane Synthesis by Aminomethylation of Guareschi Imide Salts in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
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    DOI

    http://dx.doi.org/10.1007/s10593-016-1843-5

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