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Multicomponent domino protocol for the stereoselective synthesis of novel pyrrolo[3,2-c]quinolinone hybrid heterocycles

Author:
Arumugam, Natarajan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Altaf, Mohammad, Mahalingam, S.M., Periyasami, Govindasami, Menéndez, J. Carlos, Ali Al-Aizari, Abdul Jaleel Mohammad
Source:
Tetrahedron letters 2019 v.60 no.8 pp. 602-605
ISSN:
0040-4039
Subject:
benzaldehyde, chemical structure, cycloaddition reactions, phenylalanine, quinolones, stereoselective synthesis
Abstract:
A series of structurally intriguing novel pyrrolo[3,2-c]quinolinone heterocyclic hybrids have been synthesized for the first time via a one-pot multicomponent domino reaction sequence that involves a 1,3-dipolar cycloaddition and two subsequent annulation steps. Baylis-Hillman adducts derived from various substituted benzaldehyde and methyl acrylate in presence of DABCO were used as a dipolarophiles, while the 1,3-dipole components were azomethine ylides, formed in situ from isatin derivatives and l-phenylalanine. The reaction generated five new bonds, three new rings and four contiguous stereocenters, which were created with full diastereomeric control.
Agid:
6290060