Synthesis of Pyrrole Derivatives via Cycloaddition Reaction of Reissert Hydrofluoroborate Salts with α-Bromoacrylamides. Issue 3 (4th May 2021)

• Record Type: Journal Article
• Authors: Rathod, Chirag H.; Patel, Anilkumar S.
• Is Part Of: Analytical chemistry letters. Volume 11:Issue 3(2021)
• Page Start: 289
• Page End: 302
• Publication Date: 2021-05-04
• Subjects: Reissert hydrofluoroborate salt -- Pyrrole derivatives -- Cycloaddition reaction -- α-Bromoacrylamides; Chemistry, Analytic -- Periodicals; 543.05
• DOI: 10.1080/22297928.2021.1883478
• Languages: English
• ISSNs: 2229-7928

Abstract

Abstract: An investigation of α-bromoacrylamide as a dienophile for the cycloaddition reaction of Reissert hydrofluoroborate salt of quinoline/phenanthridine has been carried out. The optimized condition has been developed for the [4+2] cycloaddition reaction of Reissert hydrofluroborate salt and α-bromoacrylamide by using K2 CO3 in DMF under moderate temperature to afford highly functionalized pyrrole derivatives (6a-f and 7a-f) in very good to excellent yield. The structures of newly synthesized compounds were established based on FT-IR, Mass, 1 H and 13 C NMR spectral techniques. Besides, the structure of compound 7a has been confirmed by 2D NMR experiments (COSY and HSQC). GRAPHICAL ABSTRACT: UF0001