Synthesis of Fused Tetracyclic Compounds via Oxidative Annulation: Access to Copper-Catalyzed Indolo[1,2- a]quinolines and to Ruthenium-Catalyzed Isoquinolin-1[2 H]-ones

Maruti Mali; Shashikant Patil; Balasubramanian Sridhar; Subhash Ghosh; Bertrand Carboni; Fabienne Berrée

doi:10.1021/acs.joc.3c00228

Synthesis of Fused Tetracyclic Compounds via Oxidative Annulation: Access to Copper-Catalyzed Indolo[1,2- a]quinolines and to Ruthenium-Catalyzed Isoquinolin-1[2 H]-ones

J Org Chem. 2023 May 5;88(9):5772-5779. doi: 10.1021/acs.joc.3c00228. Epub 2023 Apr 14.

Authors

Maruti Mali^{1

2}, Shashikant Patil^{1

2}, Balasubramanian Sridhar^{3

2}, Subhash Ghosh^{1

2}, Bertrand Carboni⁴, Fabienne Berrée⁴

Affiliations

¹ Department of Organic Synthesis and Process Chemistry, CSIR - Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
² Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
³ Department of Analytical Chemistry, CSIR - Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
⁴ Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France.

PMID: 37058287
DOI: 10.1021/acs.joc.3c00228

Abstract

A facile double oxidative annulation of (en-3-yn-1-yl)phenylbenzamides was developed allowing us to synthetize fused tetracyclic compounds. Under copper catalysis, the reaction proceeds with high efficiency and leads to new indolo[1,2-a]quinolines via a decarbonylative double oxidative annulation. On the other hand, under ruthenium catalysis, new isoquinolin-1[2H]-ones were obtained via a double oxidative annulation.