SELECTIVE SYNTHESIS OF 2-METHYLIDENEPYRROL-3-ONES FROM DIYNONES AND AMINES

Authors

  • Alena S. Pankova Saint Petersburg State University, Institute of Chemistry
  • Nadezhda D. Cherepanova Saint Petersburg State University, Institute of Chemistry
  • Pavel Golubev Saint Petersburg State University, Institute of Chemistry
  • Mikhail A. Kuznetsov Saint Petersburg State University, Institute of Chemistry

DOI:

https://doi.org/10.1007/5130

Keywords:

alkynes, diynones, enamines, pyrrolones, cyclization

Abstract

Addition of primary amines to 1-phenyl-5-trimethylsilylpenta-1,4-diyn-3-one with subsequent cyclization affords 5-phenyl-2-(trimethylsilylmethylidene)-1,2-dihydro-3H-pyrrol-3-ones. Both electron-rich and electron-deficient anilines and alkyl amines provide regio- and stereoselective formation of single product in high yields. The two-step transformation benefits from full atom economy, operational simplicity, and no need for additives and catalysts.

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Published

2019-07-23

Issue

Vol. 55 No. 7 (2019)

Section

Short Communications