A Copper‐Catalyzed Tandem Synthesis of Indolo‐ and Pyrrolo[2,1‐a]isoquinolines

Abstract

Isoquinoline ring the changes: A novel strategy for the title reaction involves ortho‐haloarylalkynes which undergo sequential intermolecular addition of N heterocycles onto alkynes and subsequent intramolecular ring closure by arylation. The process involves the use of hydroxymethyl benzotriazole as an efficient and inexpensive ligand for the CN and CC coupling reactions.

A Copper‐Benzotriazole‐Based Coordination Polymer Catalyzes the Efficient One‐Pot Synthesis of (N′‐Substituted)‐hydrazo‐4‐aryl‐1,4‐dihydropyridines from Azines

“…A similar intermediate has been supported by a previous theoretical study on the copper‐catalyzed synthesis of azoles . This hypothesis found support from related literature on Cu‐benzotriazole‐catalyzed electrophilic cyclization of N ‐arylamines, as well as Cu‐catalyzed synthesis of isoquinoline derivatives or other heteroarenes …”

Gold(I)‐Catalyzed Cascade for Synthesis of Pyrrolo[1,2‐a:2′,1′‐c]‐/Pyrido[2,1‐c]pyrrolo[1,2‐a]quinoxalinones

“…[1] In particular, gold-catalyzed cascade reactions have attracted considerable attention because of their ability to activate alkyne, alkene, and allene functionalities under mild conditions and at low catalyst loadings. [2] In recent years, significant improvements have been made in the cascade reactions catalyzed by gold complexes; however, most of the reported cascade sequences employed an intramolecular ring-closing reaction with a single starting material involving multiple functional groups strategically positioned along the chain and a terminal alkyne functionality.…”

Modern Friedel-Crafts chemistry. Part 35. New synthetic approach to substituted indolo[2,1-a][2]benzazepines and indolo[2,1-a]isoquinolines via Friedel-Crafts cyclialkylations

“…[2]benzazepine (1) 4 and 6,7-dihydroindolo[2,1-a]isoquinoline (2) [5][6][7] have unique nitrogen-containing tetracyclic 8 structures (Scheme 1). Their analogues occur widely in isolated natural products 9 , in drugs 10 and the derived π-conjugated materials are used as organic semiconductors.…”