coumarin–tetrapyrrolic macrocycle conjugates: synthesis and applications

coumarin–tetrapyrrolic macrocycle conjugates: synthesis and applications

;Ana F. R. Cerqueira;Vítor A. S. Almodôvar;Maria G. P. M. S. Neves;Augusto C. Tomé
Journal of ethnopharmacology 2017 Vol. 22 pp. 994-
155
cerqueira2017moleculescoumarintetrapyrrolic

Abstract

This review covers the synthesis of coumarin–porphyrin, coumarin–phthalocyanine and coumarin–corrole conjugates and their potential applications. While coumarin–phthalocyanine conjugates were obtained almost exclusively by tetramerization of coumarin-functionalized phthalonitriles, coumarin–porphyrin and coumarin–corrole conjugates were prepared by complementary approaches: (a) direct synthesis of the tetrapyrrolic macrocycle using formylcoumarins and pyrrole or (b) by functionalization of the tetrapyrrolic macrocycle. In the last approach a range of reaction types were used, namely 1,3-dipolar cycloadditions, hetero-Diels–Alder, Sonogashira, alkylation or acylation reactions. This is clearly a more versatile approach, leading to a larger diversity of conjugates and allowing the access to conjugates bearing one to up to 16 coumarin units.

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