Chlorinated 2-hydroxynaphthalenoxazolines: Synthesis, Reaction Mechanism and Fluorescence Properties

Author(s)

Barbeiro, Cristiane S. ; Vasconcelos, Stanley N. S. ; Zukerman-Schpector, Julio ; Caracelli, Ignez ; Pimenta, Daniel C. ; Rodrigues, Ana Clara B. ; Fernandes, Andre S. ; Correra, Thiago C. ; Bastos, Erick L. ; Stefani, Helio A.

• Document type: Journal article
• Source: CHEMISTRYSELECT; v. 1, n. 18, p. 5647-5652, NOV 1 2016.
• Web of Science Citations: 5

Abstract

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 SOCl2. 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 SCl3(+) as an electrophile is proposed. (AU)

• FAPESP's process: 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts
• Grantee: Stanley Nunes Siqueira Vasconcelos
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy
• Grantee: Thiago Carita Correra
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 15/11769-9 - Isolation of Sharpless reaction intermediates epoxidation and characterization of these species by theoretical calculations
• Grantee: André Santos Fernandes
• Support Opportunities: Scholarships in Brazil - Scientific Initiation