A Novel Approach for the Synthesis of N-Arylpyrroles

作者：Dumitrascu Florea; Georgescu Emilian; Caira Mino R^*; Georgescu Florentina; Popa Marcel; Draghici Bogdan; Dumitrescu Dan G

来源：Synlett, 2009, 2009(20): 3336-3340.

DOI：10.1055/s-0029-1218372

• 1,3-dipolar cycloaddition
• N-ylide
• pyrroles
• pyrrolo[1,2-a]quinazoline
• one-pot reaction

Treatment of quinazolin-4(3H)-one bromides with acetylenic dipolarophiles in 1,2-epoxybutane medium gave, in good yields, N-arylpyrroles instead of the corresponding pyrrolo[1,2-a] quinazolines. The structures of the pyrroles were deduced by NMR spectroscopy and confirmed by X-ray crystal structure analysis. The (1)H NMR spectra of ethyl esters revealed hindered rotation about the N-Ar bond.