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...

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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
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container_title Chemistry of heterocyclic compounds (New York, N.Y. 1965)
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creator Filippov, Igor R.
Sonina, Alina A.
Vorob’ev, Aleksey Yu
description 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.
doi_str_mv 10.1007/s10593-024-03272-9
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subjects Chemistry
Chemistry and Materials Science
Heterocyclic compounds
High temperature
Organic Chemistry
Pharmacy
Phosphonates
Room temperature
title The synthesis of indolizin-1-ylphosphonates via the reaction of ethynylphosphonates with pyridinium methylides
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