Multicomponent reactions mediated by NbCl5 for the synthesis of phthalonitrile-quinoline dyads: Methodology, scope, mechanistic insights and applications in phthalocyanine synthesis
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2018-04-01
Autores
Bartolomeu, Aloisio de A.
Brocksom, Timothy J.
da Silva Filho, Luiz C. [UNESP]
de Oliveira, Kleber T.
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Resumo
Herein, we demonstrate the efficiency of NbCl5 to promote a multicomponent reaction (MCR) for the synthesis of a library of phthalonitrile-quinoline dyads, which are very useful and new functionalized building blocks for phthalocyanine (PC) synthesis. Experimental mechanistic insights on the key MCR process are described, using a deuterated reagent, clearly showing the pericyclic nature of a hetero-Diels-Alder reaction. Examples of phthalocyanine (PC) syntheses were performed in order to demonstrate the versatility of the phthalonitrile-quinoline dyads. Preliminary photophysical measurements show that our phthalonitrile library is very promising for the production of new molecular scaffolds of PC derivatives with potential applications.
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Multicomponent reactions, NbCl5, Phthalocyanines, Phthalonitrile-quinoline dyads
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Dyes and Pigments, v. 151, p. 391-402.