A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity. Issue 24 (3rd June 2019)

• Record Type: Journal Article
• Authors: Patel, Om P. S.; Dhiman, Shiv; Khan, Shahid; Shinde, Vikki N.; Jaspal, Sonam; Srivathsa, Manu R.; Jha, Prabhat N.; Kumar, Anil
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 24(2019)
• Page Start: 5962
• Page End: 5970
• Publication Date: 2019-06-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00797k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Synthesis of 2-amidobenzoic acids has been achieved through TBHP-mediated oxidative ring opening of 2-arylindoles. The synthesized compounds have been evaluated for their antimicrobial activity. Abstract : A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert -butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a–s ) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL −1 ) and compounds2d and2p showed the maximum (32 μg mL −1 ) antifungal activity against A. flavus and C. albicans .