Porphyrins in 1,3-dipolar cycloaddition reactions. Synthesis of new porphyrin-chlorin and porphyrin-tetraazachlorin dyads.
N-(Porphyrin-2-ylmethyl)glycine was synthesized and used as precursor of azomethine ylide, which was trapped with several dipolarophiles. The reaction of that azomethine ylide with dimethyl fumarate afforded the expected adduct. However, with 1,4-benzo- and 1,4-naphthoquinones only dehydrogenated adducts were isolated. Also, the reaction of that ylide with meso-tetrakis(pentafluorophenyl)porphyrin and tetraazaporphine allowed access to novel porphyrin-chlorin and porphyrin-tetraazachlorin dyads.
Silva
Ana M G
AM
Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
Lacerda
Paula S S
PS
Tomé
Augusto C
AC
Neves
Maria G P M S
MG
Silva
Artur M S
AM
Cavaleiro
José A S
JA
Makarova
Elena A
EA
Lukyanets
Evgeny A
EA