1,3-Dipolar cycloadditions for the synthesis of low aggregation chlorins: A methodological study

1,3-Dipolar cycloadditions for the synthesis of low aggregation chlorins: A methodological study

Souza, Juliana M. de; Assis, Francisco F. de; Carvalho, Carla M. B.; Cavaleiro, José A. S.; Brocksom, Timothy J.; Oliveira, Kleber T. de

Abstract:

Porphyrins are a class of heterocyclic compounds with comprehensive applications in technology, catalysis, materials science as well as in medicine. Chlorin derivatives are natural or synthetic porphyrinoids with one of the pyrrole rings reduced at the β position. So far no synthetic approach has proven to be as efficient in producing chlorins as cycloaddition reactions. For example, five member rings formed by the 1,3-dipolar cycloadditions on porphyrins, are essential to produce compounds with low aggregation in solution, thus providing new molecules for use in photodynamic therapy (PDT) studies. Therefore, this work aims at the synthesis of new chlorin derivatives with low aggregation. Several conditions are being tested in order to provide a comprehensive study on the reactivity of dipoles (azomethine ylide) and dipolarophiles (porphyrins) under mild conditions.

Porphyrins are a class of heterocyclic compounds with comprehensive applications in technology, catalysis, materials science as well as in medicine. Chlorin derivatives are natural or synthetic porphyrinoids with one of the pyrrole rings reduced at the β position. So far no synthetic approach has proven to be as efficient in producing chlorins as cycloaddition reactions. For example, five member rings formed by the 1,3-dipolar cycloadditions on porphyrins, are essential to produce compounds with low aggregation in solution, thus providing new molecules for use in photodynamic therapy (PDT) studies. Therefore, this work aims at the synthesis of new chlorin derivatives with low aggregation. Several conditions are being tested in order to provide a comprehensive study on the reactivity of dipoles (azomethine ylide) and dipolarophiles (porphyrins) under mild conditions.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013912172320

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Como citar:

Souza, Juliana M. de; Assis, Francisco F. de; Carvalho, Carla M. B.; Cavaleiro, José A. S.; Brocksom, Timothy J.; Oliveira, Kleber T. de; "1,3-Dipolar cycloadditions for the synthesis of low aggregation chlorins: A methodological study", p-215-215. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013912172320