ONE-POT THREE-COMPONENT REACTION OF NINHYDRIN, 1,3-DICARBONYL COMPOUNDS, AND PRIMARY AMINES TO AFFORD INDENO[1,2-<i>b</i>]PYRROL-4(1<i>H</i>)-ONES

Authors

  • Zinatossadat Hossaini Department of Chemistry, Qaemshahr Branch, Islamic Azad University
  • Hossein Karami Department of Chemistry, Qaemshahr Branch, Islamic Azad University
  • Maryam Sabbaghan Department of Chemistry, Faculty of Sciences, Shahid Rajaee Teacher Training Universit
  • Faramarz Rostami-Charati Department of Chemistry, Faculty of Science, Gonbad Kavous University

DOI:

https://doi.org/10.1007/4756

Keywords:

dialkyl acetylenedicarboxylate, 1, 3-dicarbonyl compound, ninhydrin, primary amine, pyrrole, Diels–Alder reaction, three-component reaction

Abstract

A convenient one-pot three-component synthesis of indeno[1,2-b]pyrrol-4(1H)-ones has been developed. The reaction of ninhydrin, 1,3dicarbonyl compounds, and primary amines in the presence of PPh3 in MeCN at room temperature produces the respective indeno[1,2-b]pyrrol-4(1H)-ones in high yields. The synthesized pyrrole derivatives have been used in the Diels–Alder reaction with dialkyl acetylenedicarboxylates in MeCN under reflux conditions to obtain indeno[1,2-b]pyrano[3,4-d]pyrroles in high yields.

 

Downloads

Published

2018-12-12

Issue

Vol. 54 No. 11 (2018)

Section

Original Papers