The synthesis of indolizin-1-ylphosphonates via the reaction of ethynylphosphonates with pyridinium methylides

The reaction of diethyl ethynyl- and 2-phenylethynylphosphonates with pyridinium methylides generated in situ from phenacyl- and 2-ethoxy-2-oxoethylpyridinium salts by the action of a base was studied. As a result of the reaction, the corresponding diethyl indolizin-1-ylphosphonates were formed. In...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2023-12, Vol.59 (11-12), p.786-792
Main Authors: Filippov, Igor R., Sonina, Alina A., Vorob’ev, Aleksey Yu
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Heterocyclic compounds
High temperature
Organic Chemistry
Pharmacy
Phosphonates
Room temperature
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reaction of diethyl ethynyl- and 2-phenylethynylphosphonates with pyridinium methylides generated in situ from phenacyl- and 2-ethoxy-2-oxoethylpyridinium salts by the action of a base was studied. As a result of the reaction, the corresponding diethyl indolizin-1-ylphosphonates were formed. In this case, diethyl ethynylphosphonate demonstrated higher reactivity and underwent a reaction at room temperature in the K 2 CO 3 –MeCN system, while reactions with 2-phenylethynylphosphonate proceeded at elevated temperatures and resulted in lower indolizine yields.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-024-03272-9