Microwave-assisted one-pot two-step imine formation–hetero-Diels–Alder–detosylation/aromatization sequence: direct access to dibenzo[b, h][1, 6]naphthyridines. Issue 37 (14th September 2022)

• Record Type: Journal Article
• Authors: Jan, Gowsia; Kumar, Atul; Karuppasamy, Muthu; Rajput, Diksha; Slathia, Nancy; Kapoor, Kamal K.; Sridharan, Vellaisamy
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 37(2022)
• Page Start: 7472
• Page End: 7482
• Publication Date: 2022-09-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01216b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A microwave-assisted, copper-catalyzed, one-pot, two-step synthesis of benzofused[1, 6]naphthyridines is established. Abstract : A microwave-assisted, copper-catalyzed, one-pot, two-step reaction is established to access functionalized [1, 6]naphthyridines in high yields (up to 96%) starting from 2-( N -propargylamino)benzaldehydes and arylamines. This rapid and operationally simple sequential reaction allowed the construction of two new heterocyclic rings and three new (2 C–C and 1 C–N) bonds in a single synthetic operation. This reaction tolerated various electron-donating and electron-withdrawing substituents well and delivered the desired products in a shorter reaction time under microwave irradiation. This reaction proceeds through a sequential imine formation, intramolecular [4 + 2] hetero-Diels–Alder reaction, and air oxidation, followed by detosylation–aromatization steps.