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Sustainable synthesis of N-heterocycles in water using alcohols following the double dehydrogenation strategy

Author:
Maji, Milan, Chakrabarti, Kaushik, Panja, Dibyajyoti, Kundu, Sabuj
Source:
Journal of catalysis 2019 v.373 pp. 93-102
ISSN:
0021-9517
Subject:
acridines, air, dehydrogenation, quinolines, reaction mechanisms, viability, water solubility
Abstract:
The present study describes the first example of synthesis of pharmaceutically relevant N-heterocycles like substituted quinolines, acridines and 1,8-naphthyridines in water under air using alcohols in presence of a new water soluble Ir-complex. The viability and efficiency of this approach was demonstrated by the efficient synthesis of biologically active natural product (±)-galipinine and gram scale synthesis of various N-heteroaromatics. Several kinetic experiments and DFT calculations were carried out to support the plausible reaction mechanism which disclosed that this system followed a concerted outer sphere mechanism for the dehydrogenation of alcohols.
Agid:
6350320