abstract
The functionalization of halogenated thiazolo[5,4-c]isoquinolines (TzIQ) through the Suzuki-Miyaura reaction with arylboronic acids is reported here for the first time. Three TzIQ derivatives bearing only chlorine atoms or chlorine and bromine atoms were used in this work. The results unequivocally confirm the impact of different halogen atoms, and their positions on the TzIQ core, on the outcome of these reactions. Excellent chemoselectivity was observed for the TzIQ bearing chlorine and bromine atoms. The new TzIQ derivatives were fully characterized by NMR and MS techniques and the structure of the TzIQ 9b was also confirmed by single-crystal X-ray diffraction. The absorption and emissive properties of the new compounds indicate that some of them may be useful in applications requiring strong luminescence and large Stokes shifts.
keywords
THIAZOLOISOQUINOLINES; PROTODEBORONATION; ACIDS
subject category
Chemistry
authors
Costa, LD; Guieu, S; Faustino, MAF; Tomé, AC
our authors
Letícia D. Costa
PhD Student
Samuel Jacques André Guieu
Junior Researcheracknowledgements
This work received financial support from the University of Aveiro and FCT/MCTES (Fundacao para a Ciencia e a Tecnologia and Ministerio da Ciencia, Tecnologia e Ensino Superior) to support the LAQV- REQUIMTE (LA/P/0008/2020 DOI 10.54499/LA/P/0008/2020, UIDP/50006/2020 DOI 10.54499/UIDP/50006/2020 and UIDB/50006/2020 DOI 10.54499/UIDB/50006/2020) research unit through national funds and, where applicable, was co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project N degrees 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC) .