Synthesis of Luotonin and Rutaecarpine Analogues by One‐Pot Intramolecular Dehydrogenative Cross‐Coupling and Benzylic C−H Oxidation, and In Vitro Cytotoxicity Assay

Abstract

Herein, we reported an effective one‐pot protocol to synthesize quinazolinone fused N‐heterocyclic scaffold, structurally similar to the natural product Luotonin and Rutaecarpine by Pd(OAc)2/Ag(OAc)‐promoted intramolecular dehydrogenative cross‐coupling (DCC). The structure of all the compounds has been confirmed unambiguously by NMR, mass, and XRD. The electronic effect of the substituents attached to the backbone of the starting material was thoroughly investigated. The outcome of the reaction is highly dependent on the substrate structure and pH of the medium. Based on the experimental observation, a probable mechanism has been proposed. To see the anti‐cancer properties, we have studied concentration‐dependent cell viability assay of one compound on SiHa cell, a human cervical cancer cell line. The observed IC50 value was 23 μM.