SYNTHESIS OF 2-[2-ISOPROPYL-4-(<i>o</i>-METHOXYPHENYL)TETRAHYDROPYRAN-4-YL]AMINE AND ITS REACTION WITH AROMATIC ALDEHYDES

Authors

  • Н. С. Арутюнян A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
  • Л. А. Акопян A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
  • Н. З. Акопян A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
  • Г. А. Геворгян A. L. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
  • Г. А. Паносян Center of Research on the Structure of Molecules, National Academy of Sciences of the Republic of Armenia

DOI:

https://doi.org/10.1007/3035

Keywords:

[2-isopropyl-4-(o-methoxyphenyltetrahydropyran-4-yl)]acetonitrile, 2-isopropyltetrahydro-pyran-4-one, derivatives of 2-[2-isopropyl-4-(o-methoxyphenyl)tetrahydropyran-4-yl]ethylamine, ethyl (2 isopropyl-4-tetrahydropyranylidene)cyanoacetate, reduction, deethoxycarbonylation

Abstract

A preparative method was developed for the synthesis of 2-isopropyltetrahydropyran-4-one, which was then transformed by the action of ethyl cyanoacetate into ethyl (2-isopropyl-4-tetrahydro-pyranylidene)cyanoacetate. Reaction of the latter with o-methoxyphenylmagnesium bromide followed by saponification and reduction with LiAlH4 led to 4-(2-aminoethyl)-2-isopropyl-4-(o-methoxy-phenyl)tetrahydropyran. A series of new azomethines, which are reduced to the corresponding amines by the action of NaBH4, were synthesized by the reaction of the above-mentioned amine with aromatic aldehydes.

How to Cite
Arutjunyan, N. S.; Hakobyan, L. H.; Hakobyan, N. Z.; Gevorgyan, G. A.; Panosyan, H. A. Chem. Heterocycl. Compd. 2010, 46, 670. [Khim. Geterotsikl. Soedin. 2010, 838.]

For this article in the English edition see DOI 10.1007/s10593-010-0567-1

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Published

2016-02-09

Issue

No. 6 (2010)

Section

Original Papers