Synthesis of stable, sparsely substituted chlorins

ORGN 931

Marcin Ptaszek, mptasze@ncsu.edu, Brian E. McDowell, bemcdowe@unity.ncsu.edu, and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204
Chlorins bearing few or no substituents are valuable benchmarks for spectroscopic characterization and fundamental studies of reactivity. Several routes were investigated for the preparation of chlorins bearing only a 10-substituent or lacking any meso- or beta-pyrrolic substituents. The synthetic approach required preparation of the appropriately functionalized tetrahydrodipyrrin (1, Western half) and dipyrromethane (2, Eastern half). The best method entailed condensation of a 2,3,4,5-tetrahydro-1,3,3-trimethyldipyrrin (1, X = H) and a 9-bromo-1-formyldipyrromethane (2, Y = CHO, Z = Br).