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- Title
Palladium-catalyzed amination in the synthesis of nitrogen and oxygen heterocycles containing fragments of cholane and quinoline.
- Authors
Averin, A. D.; Uglov, A. N.; Ranyuk, E. R.; Lukashev, N. V.; Beletskaya, I. P.
- Abstract
By Mitsunobu reaction from 3,24-cholanediol and 2-hydroxy-8-chloroquinoline 24-(8-chloroquinolinyl-2-oxy)cholan-3-ol and 3,24-di(8-chloroquinolinyl-2-oxy)cholane were synthesized. These compounds were brought into reactions of palladium-catalyzed amination with propanediamine, oxaalkane diamines, and N,N′-bis(3-aminopropyl)ethylenediamine to obtain macrocycles of various structures, linear mono- and bis(steroid) derivatives of trioxaalkane diamine, and also cholane bis(oxaalkandiamine) derivative. The dependence was demonstrated of macrocyles and cyclooligomers yield on the polyamine nature. 4-Hydroxy-7-chloroquinoline afforded only 24-(7-chloroquinolinyl-4-oxy)cholan-3-ol.
- Subjects
PROPANEDIAMINE; ETHYLENEDIAMINE; AMINATION; QUINOLINE; POLYAMINES; MACROCYCLIC compounds
- Publication
Russian Journal of Organic Chemistry, 2009, Vol 45, Issue 2, p273
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428009020213