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Chlorinated 2‐hydroxynaphthalenoxazolines: Synthesis, Reaction Mechanism and Fluorescence Properties
Author(s) -
Barbeiro Cristiane S.,
Vasconcelos Stanley N. S.,
ZukermanSchpector Júlio,
Caracelli Ignez,
Pimenta Daniel C.,
Rodrigues Ana Clara B.,
Fernandes André S.,
Correra Thiago C.,
Bastos Erick L.,
Stefani Hélio A.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601526
Subject(s) - halogenation , electrophile , chemistry , fluorescence , reaction mechanism , coupling reaction , mass spectrometry , surface modification , combinatorial chemistry , photochemistry , organic chemistry , chromatography , catalysis , physics , quantum mechanics
A chlorinated 2‐HNO (2‐hydroxynaphthalenoxazoline) was synthesized by an ultrasound‐assisted coupling reaction between 1‐hydroxy‐2‐naphthoic acid and L‐threonine followed by simultaneous halogenation and cyclization with inversion of configuration using excess SOCl 2 . Further functionalization of 2‐HNO led to a small library of slightly fluorescent amides or esters in 55–81 % yields. Quantum chemical calculations combined with high‐resolution mass spectrometry analysis were used to rationalize the mechanism of reaction, and the formation of SCl 3 + as an electrophile is proposed.