Photoredox synthesis of functionalized quinazolines via copper-catalyzed aerobic oxidative Csp2–H annulation of amidines with terminal alkynes. Issue 14 (9th July 2021)

• Record Type: Journal Article
• Authors: Charpe, Vaibhav Pramod; Ragupathi, Ayyakkannu; Sagadevan, Arunachalam; Hwang, Kuo Chu
• Is Part Of: Green chemistry. Volume 23:Issue 14(2021)
• Page Start: 5024
• Page End: 5030
• Publication Date: 2021-07-09
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d1gc01493e
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : We demonstrate a simple CuCl-catalyzed C–H annulation of amidines with terminal alkynes to form functionalized quinazolines at RT. This photochemical method is a mild process, highly efficient, and practically applicable to the synthesis of anticancer agents. Abstract : We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp 2 –H annulation (Friedel–Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copper(i )-phenylacetylide catalyzed photo-oxidative Csp 2 –H annulation of amidines at RT, which is very challenging and complementary to the conventional transition metal-catalyzed thermal annulation reactions. We have demonstrated the application of this method by synthesizing anti-cancer compounds. Moreover, green chemistry metrics (the E -factor is ∼1.9 times better than that of the reported thermal method) and Eco-Scale (scales 55.4, which shows an acceptable synthesis) evaluations show that this method is eco-friendly and environmentally feasible.