1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones

Hélio M.T. Albuquerque, Clementina M.M. Santos, Mannix P. Balanay, José A.S. Cavaleiro, Artur M.S. Silva

Research output: Contribution to journalArticle

Abstract

The 1,6-conjugate addition of nitromethane to 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones was accomplished and led mainly to the corresponding β-(nitromethyl)chromones. (E)-5′-(Nitromethyl)-3′-styryl-[1,1′-biphenyl]-2-ol and 3′-aryl-2′-nitro-5′-(nitromethyl)spiro[chromane-2,1′-cyclohexan]-4-one derivatives were also isolated as minor products from tandem processes, which result from the addition of a second molecule of nitromethane. The nucleophile scope was investigated with malononitrile, acetylacetone, ethyl cyanoacetate, and diethyl malonate, which gave the expected 1,6-addition products; in the last case, it was also possible to isolate a minor product formed through a 1,8-/1,6-addition sequence. Computational calculations provided a rationale for the experimental reactivity of carbon nucleophiles with 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones. The further functionalization of some adducts allowed the preparation of new nitrogen-containing heterocyclic compounds, such as new styrylpyrrolidines and new pyrazole and bis(pyrazole) derivatives.

Original languageEnglish
Pages (from-to)5293-5305
Number of pages13
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number35
DOIs
Publication statusPublished - Sep 25 2017

Keywords

  • Conjugate addition
  • Density functional calculations
  • Nitrogen heterocycles
  • Oxygen heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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