Nitrogen bridgehead compounds. Part 74. Cyclization of 2-(2- pyridylaminomethylene)succinates in ethanolic sodium ethoxide. Part 2. Michael addition of pyridyldihydropyrrolones

Lelle Vasvári-Debreczy, István Hermecz, Benjamin Podányi, Tünde Erös-Takácsy

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2 Citations (Scopus)

Abstract

2-(2-Pyridylaminomethylene)succinates, which in ethanolic sodium ethoxide solution yielded equilibrium mixtures of the pyridopyrimidines (3) and the pyridyldihydropyrrolones (5) and (6), within 15 min, furnished a dihydropyrrolone dimer as the main product on longer (≥2 h) reaction. The dimer had the unusual 4,4'-connection between the five-membered rings, and was shown to be the pure transdiastereoisomer (7); it is considered to be formed by a Michael addition reaction of the pyrrolones (5) and (6). These longer reactions are accompanied by hydrolytic processes.

Original languageEnglish
Pages (from-to)2019-2022
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
DOIs
Publication statusPublished - Jan 1 1988

ASJC Scopus subject areas

  • Chemistry(all)

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