STRATEGY FOR THE SYNTHESIS OF 2,2-DISUBSTITUTED 8-AZACHROMANONES <i>VIA</i> HORNER–WADSWORTH–EMMONS OLEFINATION

Authors

  • Taras V. Omelian Enamine Ltd.; Taras Shevchenko National University of Kyiv
  • Eugeniy N. Ostapchuk Enamine Ltd.; Taras Shevchenko National University of Kyiv
  • Alexey V. Dobrydnev Enamine Ltd.; Taras Shevchenko National University of Kyiv
  • Yehor S. Malets Enamine Ltd.; V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine
  • Volodymyr S. Brovarets V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine
  • Oleksandr O. Grygorenko Enamine Ltd.; Taras Shevchenko National University of Kyiv

DOI:

https://doi.org/10.1007/5450

Keywords:

azachromanone, phosphonate, cyclization, Horner–Wadsworth–Emmons reaction, olefination, protecting group.

Abstract

A series of 2,2-disubstituted 8-azachromanones, including spirocyclic compounds, have been synthesized via Horner–Wadsworth–Emmons reaction. Dimethyl methylphosphonate was acylated with methyl 2-methoxypyridine-3-carboxylate to afford the key intermediate – dimethyl [2-(2-methoxypyridin-3-yl)-2-oxoethyl]phosphonate. Further reaction of this phosphonate and ketones followed by treatment with TMSCl–NaI provided the target 8-azachromanones. Scope and limitations of the developed synthetic method have been investigated.

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Published

2020-02-28

Issue

Vol. 56 No. 2 (2020)

Section

Original Papers