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Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3 H )‐ones in Water
Author(s) -
Dandia Anshu,
Sharma Ruchi,
Indora Aayushi,
Parewa Vijay
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801224
Subject(s) - chemistry , combinatorial chemistry , regioselectivity , hydrogen bond , aqueous solution , catalysis , computational chemistry , photochemistry , molecule , organic chemistry
A novel water assisted strategy has been developed for the synthesis of quinazolinones by the reaction of o ‐aminobenzamides 1 with benzyl alcohols 2 using NaCl in regioselective manner under microwave radiation (MW). NaCl and water plays an unprecedented and vital role in the reaction. NaCl create more space for the reactants in aqueous media and bring them in very close proximity for C−N bond formation through “kosmotropes perturbation”. There is no need of any metal, ligand and base for further activation of the reactants in the reaction because water trigger the reaction via “ambiphilic dual activation” of reactants through hydrogen bond accepter and donor ability in the pertinent C−N bond forming steps in the reaction. This “kosmotropes perturbation” and “ambiphilic dual activation” is the accountable attribute for making a new water‐assisted strategy. Several controlled experiments have been carried out to establish the suitable mechanism and stipulation of the reactions. The process illustrated significant selectivity for quinazolinones over dihydrogenated quinazolinones.