Synthesis of Cycloalk[b]indole Bearing Spiropiperidine Derivatives

Abstract

in Wiley Online Library (wileyonlinelibrary.com).The novel heterocyclic compounds that have cycloalk [b]indole moiety bearing spiropiperidinone and spiropiperidinedione (3a, 3b, 3c, 5a, 5b, 8a, 8b, and 10a) were synthesized for the first time. The synthesis of spiropiperidinone and spiropiperidinedione structures was performed by a new method. These compounds are similar to sedative and hypnotic drugs such as methyprylon, glutethimide, and thalidomide.

Regioselective Hydrogenolysis of Donor–Acceptor Cyclopropanes with Zn-AcOH Reductive System

“…A rapid access to tetralins and their heterocyclic analogs can be provided via S E Ar in the cases when 2 contains an electron-abundant (het)­aryl substituent. , Thus, carbazole derivative 5 was obtained directly from indolylmalonate 2u in a good yield (Scheme ).…”

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

“…This domino Michael/intramolecular N-acylation methodology could be extended to combinations of cyclic -ketoesters fused to N-methylindoles 5e and acrylamide (1a), as demonstrated by Ergün and co-workers (upper part of Scheme 4). 18 The reaction was carried out in absolute methanol employing sodium methoxide as a base to generate the intermediate enolate anion 10. The reaction efficiency was largely affected by the substrate ring size (n = 0-2), the targeted polycyclic systems 6e being isolated from low (n = 2: 15%) to good (n = 0: 64% and n = 1: 69%) yields.…”

“…Along these lines, Michael additions telescoped with an intramolecular enamide formation resembling the above studies (Schemes 5 and 6) [15][16][17][18] were investigated by various research teams, mostly motivated by structure-activity relationship (SAR) studies (Table 1). 24,25 Reaction in a basic medium with ketones 13a presumably generates in situ the corresponding enolates or enamines as precursors of the 1,4-addition products 17, the amidic nitrogen atom of which then promotes intramolecular condensation to the ketone forming an enamide.…”