Leveraging cascade alkynyl Prins cyclization towards the stereoselective synthesis of spiro-furan quinazolinone scaffolds

Chem Commun (Camb). 2023 Nov 30;59(96):14301-14304. doi: 10.1039/d3cc04464e.

Abstract

A TfOH-promoted, metal-free protocol has been unveiled for the synthesis of spiro-furan quinazolinones employing alkynol urea derivatives utilizing alkynyl Prins cyclization reaction. This methodology produces highly functionalized spiro-heterocycles in excellent yields with exclusive E-selectivity under ambient conditions. Furthermore, late-stage modifications incorporate bromide and acetyl functionalities into the synthesized spiro-heterocycles.