REACTION OF DIKETENE WITH CYANOTHIOACETAMIDE: A CONVENIENT AND REGIOSELECTIVE METHOD FOR THE PREPARATION OF NEW 4(1H)-PYRIDONE DERIVATIVES

Authors

  • В. В. Доценко "ChemEx" Laboratory, Vladimir Dal East-Ukrainian National University, 91034 Lugansk
  • С. Г. Кривоколыско "ChemEx" Laboratory, Vladimir Dal East-Ukrainian National University, 91034 Lugansk
  • В. П. Литвинов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow
  • А. Н. Чернега Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02094 Kiev

DOI:

https://doi.org/10.1007/7525

Keywords:

diketene, 4(1H)-pyridones, 5H-pyrido[2', 3', 4, 5]thiopyrano[2, 3-b]pyridines, thiazolo-[3, 2-a]pyridines, thieno[2, cyanothioacetamide, S-alkylation, X-ray diffraction structural analysis, Thorpe-Ziegler cyclization, cyclocondensation

Abstract

The reaction of diketene with cyanothioacetamide in dry dioxane in the presence of triethylamine gives triethylammonium 3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinethiolate. The  regioselective S-alkylation  of this thiolate is a convenient method for the preparation of substituted 4(1H)-pyridones and also derivatives of thiazolo[3,2-a]pyridine and thieno[2,3-b]pyridine. The  action  of 2-amino-1,1,3-tricyanopropene on this thiolate leads to  its transformation into a new heterocyclic system, namely, 5H-pyrido[2',3':4,5]thiopyrano[2,3-b]pyridine; treatment with iodine yields  the oxidation product, namely, the corresponding  bis(2-pyridyl) disulfide. The structure of isopropyl (3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinyl)thioacetate  was confirmed by X-ray diffraction structural analysis.

How to Cite
Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, B. P.; Chernega, A. N.  Chem. Heterocycl. Compd. 2007, 43, 599. [Khim. Geterotsikl. Soedin. 2007, 716.]

For this article in the English edition see DOI 10.1007/s10593-007-0094-x


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Published

2023-03-21

Issue

No. 5 (2007)

Section

Original Papers