Author:
Cimarelli Cristina,Palmieri Gianni,Volpini Emanuela
Abstract
A facile and simple method for the preparation of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones or naphthoxazin-2-ones in high yields from aminoalkylphenols and aminoalkylnaphthols is described. The reactions of the products obtained with organolithium and Grignard reagents were studied, and a method for the preparation of N-[1-(2-hydroxyphenyl)alkyl]-N-alkylamides, which are of pharmaceutical interest, from benzoxazinones was developed. A possible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of 1H NMR spectra.Key words: benzoxazinones, naphthoxazinones, organometallic reagents, amide preparation, aminoalkylphenols.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
24 articles.
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1. 3,4-Dihydro-2H-1,3-benzoxazines and their oxo-derivatives - Chemistry and bioactivities;Journal of the Serbian Chemical Society;2021
2. Development of N,N-disulfo-1,1,3,3-tetramethylguanidinium chlorometallates as heterogeneous catalysts for one pot synthesis of 1,2-dihydro-1-aryl-3H-naphth[1, 2-e][1,3]oxazin-3-one derivatives;Current Organocatalysis;2020-07-21
3. ompg-C3N4/SO3H organocatalyst-mediated green synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3] oxazin-3-ones under solvent-free and mild conditions: a fast and facile one-pot three-component approach;Monatshefte für Chemie - Chemical Monthly;2020-05
4. Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines;Organic Letters;2019-02-15
5. A One-Pot Multicomponent Synthesis of Naphthoxazin-3-one Derivatives Using Amberlite IRA-400 Cl Resin as Green Catalyst;Letters in Organic Chemistry;2018-06-13