Synthesis and structure of 7-alkoxyalkyl-3-thia-7-zabicyclo[3.3.1]nonan-9-ones and several of their derivatives |
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Authors: | V. K. Yu K. D. Praliev E. E. Fomicheva R. D. Mukhasheva S. G. Klepikova |
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Affiliation: | (1) Institute of Chemical Sciences, Ministry of Science and Education Republic of Kazakhstan, 480100 Almaty, Kazakhstan |
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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. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 585–592, April, 2006. |
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Keywords: | 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-one and its derivatives synthesis 13C NMR spectra structure pharmacological properties |
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