Syntheses of 2-Benzylbenzofuran Derivatives and 2-Aryl-nitrochroman Derivatives from Nitroalkene Precursors

Chia Yu Huang, Chun Wei Kuo, Veerababurao Kavala, Ching Fa Yao

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Simple and straightforward methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH4 followed by a Nef reaction and acid-mediated cyclization, whereas 3-substituted 2-benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid-mediated cyclization in a one-pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4-diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β-(2-hydroxyphenyl)-nitroethanes and benzaldehydes, also in a one-pot process. Simple and convenient methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described.

Original languageEnglish
Pages (from-to)2720-2734
Number of pages15
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number15
DOIs
Publication statusPublished - 2016 May 1

Keywords

  • Cyclization
  • Nef reaction
  • Nitroalkenes
  • Oxygen heterocycles
  • Synthesis design

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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