[Ag(PcL)]‐Catalyzed Domino Reactions of 2‐Alkynylbenzaldehydes with Electron‐Poor Anilines: Synthesis of 1‐Aminoisochromenes. Issue 17 (15th April 2020)

• Record Type: Journal Article
• Authors: Pirovano, Valentina; Hamdan, Gabriele; Garanzini, Davide; Brambilla, Elisa; Rossi, Elisabetta; Caselli, Alessandro; Abbiati, Giorgio
• Is Part Of: European journal of organic chemistry. Issue 17(2020)
• Page Start: 2592
• Page End: 2599
• Publication Date: 2020-04-15
• Subjects: Isochromenes -- Alkynes -- Domino reactions -- Silver -- Electron‐poor anilines -- Macrocyclic ligands; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000275
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : In this paper, we describe the synthesis of neglected 1‐aminoisochromene derivatives starting from 2‐alkynylbenzaldehydes and electron‐poor anilines. The domino reaction is catalyzed by original [Ag I PcL] complexes and occurs with complete regioselectivity under mild conditions. The approach well‐tolerates different aryl, heteroaryl, alkyl and cycloalkyl substituents on alkyne terminus to give the desired products in modest to very good yields. Abstract : A series of neglected 1‐aminoisochromenes have been prepared under mild condition by a selective domino reaction between 2‐alkynylbenzaldehydes and electron‐poor anilines catalyzed by original silver(I) complexes characterized by the presence of a pyridine containing macrocyclic ligand [Ag I PcL].