N-Aryl-2-hydroxy-1,2,3,4-tetrahydropyridines and N-aryl-2-chloromethylene-1,2,3,4-tetrahydropyridines — successive intermediates in the Hantzsch synthesis of 1,4-dihydropyridines

Authors

  • Б. Чекавичус Latvian Institute of Organic Synthesis, Riga LV-1006
  • Ю. Попелис Latvian Institute of Organic Synthesis, Riga LV-1006
  • Е. Шебенина Latvian Institute of Organic Synthesis, Riga LV-1006
  • А. Саусиньш Latvian Institute of Organic Synthesis, Riga LV-1006
  • P. Верхе Latvian Institute of Organic Synthesis, Riga LV-1006
  • Г. Дубурс Latvian Institute of Organic Synthesis, Riga LV-1006

Abstract

Esters of 4-chloro-2-arylideneacetoacetic acid I and esters of N-arylaminocrotonic acid II form stable N-aryl-3,4-trans-2-hydroxy-1,2,3,4-tetrahydropyridines III. Their regio- and stereoselective dehydration results in N-aryl-2-chloromethylene-1,2,3,4-tetrahydropyridines with an exocyclic bond, IV. Compounds IV isomerize to the corresponding N-aryl-2-chloromethyl-1,4-dihydropyridines V in acid medium. Michael addition of compounds I and II in chloroform or benzene forms carbocyclic derivatives of cyclohexene VI.

How to Cite
Chekavichus, B.; Popelis, Y.; Shebenina, E; Sausin'sh, A.; Verkhe, R.; Duburs, G. Chem. Heterocycl. Compd. 1997, 33, 799. [Khim. Geterotsikl. Soedin. 1997, 915.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02253029

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Published

1997-07-25

Issue

No. 7 (1997)

Section

Original Papers