Reaction of cytisine with alka-1,3- and -2,3-dien-2-ylphosphonates
Methods have been developed for functionalizing the alkaloid cytisine via introduction of alka-1,3- and -2,3-dien-2-ylphosphonate fragments. The main pathway of the reaction of cytisine with 2-(diethoxyphosphoryl) alka-2,3-dien-1-yl methanesulfonates is nucleophilic substitution of the methanesulfon...
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Published in | Russian journal of organic chemistry Vol. 52; no. 12; pp. 1804 - 1811 |
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Main Author | |
Format | Journal Article |
Language | English |
Published |
Moscow
Pleiades Publishing
01.12.2016
Springer Nature Springer Nature B.V |
Subjects | |
Online Access | Get full text |
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Summary: | Methods have been developed for functionalizing the alkaloid cytisine via introduction of alka-1,3- and -2,3-dien-2-ylphosphonate fragments. The main pathway of the reaction of cytisine with 2-(diethoxyphosphoryl) alka-2,3-dien-1-yl methanesulfonates is nucleophilic substitution of the methanesulfonyloxy group with retention of the alkadiene skeleton. A minor reaction pathway is nucleophilic substitution with formation of alka-1,3-dien-2-ylphosphonates. Cytisine conjugates with exclusively alka-1,3-dien-2-ylphosphonate fragment have been synthesized by copper(I)-catalyzed 1,3-dipolar cycloaddition of
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-(prop-2-yn-1-yl)cytisine to 3-azidoalka-1,3-dien-2-ylphosphonates. |
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ISSN: | 1070-4280 1608-3393 |
DOI: | 10.1134/S1070428016120162 |