Substituted pyrrole synthesis from nitrodienes Academic Article uri icon

Overview

MeSH Major

  • Pulmonary Disease, Chronic Obstructive
  • Smoking
  • Wnt Proteins
  • beta Catenin

abstract

  • © 2017 Elsevier Ltd.Though the Cadogan-Sundberg approach has been employed to synthesize a variety of indole and carbazole derivatives from nitroarenes, surprisingly, very little is reported for making pyrroles using the same approach from non-arene nitrodienes. Herein, we report a general method to synthesize substituted pyrroles, in one step with modest yields, from nitrodienes using triphenylphosphine in the presence of an Mo catalyst, bis(acetylaceto)dioxomolybdenum (VI). To shed light on the mechanism of this reaction, we performed DFT calculations using uB3LYP/6-31+G(d) basis set and observed that the reaction favors a path through a nitrene intermediate.

publication date

  • January 25, 2017

Research

keywords

  • Academic Article

Identity

Digital Object Identifier (DOI)

  • 10.1016/j.tetlet.2017.04.077

Additional Document Info