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 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Moscow
Pleiades Publishing
01.12.2016
Springer Nature Springer Nature B.V |
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| Abstract | 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
N
-(prop-2-yn-1-yl)cytisine to 3-azidoalka-1,3-dien-2-ylphosphonates. |
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| AbstractList | 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 N-(prop-2-yn-1-yl)cytisine to 3-azidoalka-1,3-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 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 N -(prop-2-yn-1-yl)cytisine to 3-azidoalka-1,3-dien-2-ylphosphonates. |
| Author | Brel, V. K. |
| Author_xml | – sequence: 1 givenname: V. K. surname: Brel fullname: Brel, V. K. email: v_brel@mail.ru organization: Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Institute of Physiologically Active Compounds, Russian Academy of Sciences |
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| CitedBy_id | crossref_primary_10_1107_S2056989023001950 crossref_primary_10_1016_j_molstruc_2021_130487 crossref_primary_10_1016_j_mencom_2018_11_031 crossref_primary_10_2174_1389557519666191104121821 |
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| Snippet | 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... |
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| Title | Reaction of cytisine with alka-1,3- and -2,3-dien-2-ylphosphonates |
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