SYNTHESIS AND STRUCTURE OF 7-ALKOXYALKYL-3-THIA-7-AZABICYCLO[3.3.1]NONAN-9-ONES AND SEVERAL OF THEIR DERIVATIVES

Authors

  • В. К. Ю Institute of Chemical Sciences, Ministry of Science and Education, Republic of Kazakhstan, 480100 Almaty
  • К. Д. Пралиев Institute of Chemical Sciences, Ministry of Science and Education, Republic of Kazakhstan, 480100 Almaty
  • Е. Е. Фомичева Institute of Chemical Sciences, Ministry of Science and Education, Republic of Kazakhstan, 480100 Almaty
  • Р. Д. Мухашева Institute of Chemical Sciences, Ministry of Science and Education, Republic of Kazakhstan, 480100 Almaty
  • С. Г. Клепикова Institute of Chemical Sciences, Ministry of Science and Education, Republic of Kazakhstan, 480100 Almaty

DOI:

https://doi.org/10.1007/8009

Keywords:

7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-one and its derivatives, synthesis, 13 C NMR spectra, structure, pharmacological properties

Abstract

New 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-ones were synthesized by the double Mannich cyclization of tetrahydrothiopyran-4-one with suitable alkoxyalkylamines and paraformaldehyde in acetous methanol. Wolff–Kishner decarbonylation of these bicyclic ketones gave 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonanes. The reduction of 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-ones by alkali metal hydride complexes leads to a mixture of two stereoisomeric secondary alcohols, which are epimers at C(9). Active analgesic, antiarrhythmic, and antibacterial compounds were found among these products.

How to Cite
Yu, V. K.; Praliev, K. D.; Fomicheva, E. E.; Mukhasheva, R. D.; Klepikova, S. G.  Chem. Heterocycl. Compd. 2006, 42, 512. [Khim. Geterotsikl. Soedin. 2006, 585.]

For this article in the English edition, see DOI 10.1007/s10593-006-0119-x


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Published

2023-08-30

Issue

No. 4 (2006)

Section

Original Papers