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...

Full description

Saved in:
Bibliographic Details
Published inRussian journal of organic chemistry Vol. 52; no. 12; pp. 1804 - 1811
Main Author Brel, V. K.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.12.2016
Springer Nature
Springer Nature B.V
Subjects
Chemical reactions
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Science & Technology
RECEPTOR SUBTYPES
LIGANDS
PHARMACOLOGICAL EVALUATION
DERIVATIVES
DIALKYL ESTERS
Online AccessGet full text

Cover

More Information
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 N -(prop-2-yn-1-yl)cytisine to 3-azidoalka-1,3-dien-2-ylphosphonates.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428016120162