Multicomponent Synthesis of Substituted and Fused-Ring Imidazoles via Phospha-münchnone Cycloaddition

2015/02/17 by Sara Aly, Mikhail Romashko, Bruce A. Arndtsen · 2 citations
Chemistry · #Catalytic C–H Functionalization Methods #Click Chemistry and Applications #Synthesis and Catalytic Reactions

paper · doi:10.1021/jo5028936

openalex publication_date 2015/02/17 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/16

Abstract

A new, one-pot synthesis of imidazoles from imines, acid chlorides, and N-nosyl imines or tethered nitriles is reported. The reaction is mediated by the phosphonite PPh(catechyl) and proceeds via regioselective cycloaddition with an in situ-generated phospha-münchnone 1,3-dipole. This provides an efficient route to construct both highly substituted and polycyclic imidazoles directly from available substrates, without metal catalysts, and with access to product diversity.

Citations

• Modular Mesoionics: Understanding and Controlling Regioselectivity in 1,3-Dipolar Cycloadditions of Münchnone Derivatives
• Cyclic 1,3-Dipoles or Acyclic Phosphonium Ylides? Electronic Characterization of “Montréalones”
• Phospha-Münchnones: Electronic Structures and 1,3-Dipolar Cycloadditions
• A New Use of Wittig-Type Reagents as 1,3-Dipolar Cycloaddition Precursors and in Pyrrole Synthesis
• Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry
• Münchnones—New Facets after 50 Years

Cited by

• Multicomponent Coupling Approach to Cross-Conjugated Polymers from Vanillin-Based Monomers
• Montréalone [wikipedia]