Russian Chemical Bulletin

, 57:2139 | Cite as

Functional sulfur-containing compounds

14. Study of intramolecular cyclization of 2-organylthio-, 2-organylsulfinyl-, and 2-organylsulfonylnicotinic acid esters and nitriles upon action of a base
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Abstract

The Thorpe-Ziegler intramolecular cyclization of 2-RCH2S-, 2-RCH2S(O)-, and 2-RCH2SO2-substituted nicotinic acid esters and nitriles (R is alkyl, aryl, and 2-thienyl) upon the action of potassium tert-butoxide has been studied. The reaction results in the formation of the corresponding 2-R-substituted 3-aminothieno[2,3-b]pyridines, 3-aminothieno[2,3-b]pyridine 1-oxides, and 3-aminothieno[2,3-b]pyridine 1,1-dioxides with the reaction taking place only in the case if R is aryl or 2-thienyl. Methyl esters of 2-RCH2S-, 2-RCH2S(O)-, and 2-RCH2SO2-substituted nicotinic acids also undergo the intramolecular cyclization of the Dieckmann type to form the corresponding 2-R-substituted 3-hydroxythieno[2,3-b]pyridines, thieno[2,3-b]pyridin-3(2H)-one 1-oxides, and thieno[2,3-b]pyridin-3(2H)-one 1,1-dioxides. Such a reaction takes place for all the R groups except when R = AlkCH2S and AlkCH2S(O).

Key words

intramolecular cyclization the Thorpe-Ziegler reaction potassium tert-butoxide 3-cyano-4,6-dimethylpyridine-2-thione methyl 4,6-dimethyl-2-thioxopyridine-3-carboxylate 4,6-dimethyl-2-organylthio-3-cyanopyridines 4,6-dimethyl-2-organylsulfinyl-3-cyanopyridines 4,6-dimethyl-2-organylsulfonyl-3-cyanopyridines 3-amino-2-[aryl(2-thienyl)]thieno[2,3-b]pyridines 3-amino-2-[aryl(2-thienyl)]thieno[2,3-b]pyridine 1-oxides 3-amino-2-[aryl(2-thienyl)]thieno[2,3-b]pyridine 1,1-dioxides 2-aryl-3-hydroxy-4,6-dimethylthieno[2,3-b]pyridine 2-aryl-4,6-dimethylthieno[2,3-b]pyridin-3(2H)-one 1-oxides 2-[aryl(butyl)]-4,6-dimethylthieno[2,3-b]pyridin-3(2H)-one 1,1-dioxides 
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Copyright information

© Springer Science+Business Media, Inc.  2008

Authors and Affiliations

  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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