THE SYNTHESIS OF INDOLIZIN-1-YLPHOSPHONATES <i>VIA</i> THE REACTION OF ETHYNYLPHOSPHONATES WITH PYRIDINIUM METHYLIDES

Authors

  • Igor R. Filippov N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Alina А. Sonina N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Aleksey Yu. Vorob'ev N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090

Keywords:

ethynylphosphonates, indolizine, indolizin-1-ylphosphonates, pyridinium methylides, [3+2] cycloaddition

Abstract

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 K2CO3–MeCN system, while reactions with 2-phenylethynylphosphonate proceeded at elevated temperatures and resulted in lower indolizine yields.

Author Biography

Aleksey Yu. Vorob'ev, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090

Заведующий лабораторией фотоактивируемых процессов НИОХ СО РАН

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Published

2024-01-10

Issue

Vol. 59 No. 11/12 (2023)

Section

Original Papers