Synthesis of 1-formyldipyrromethanes

Marcin Ptaszek; Brian E McDowell; Jonathan S Lindsey

doi:10.1021/jo060119b

Synthesis of 1-formyldipyrromethanes

J Org Chem. 2006 May 26;71(11):4328-31. doi: 10.1021/jo060119b.

Authors

Marcin Ptaszek¹, Brian E McDowell, Jonathan S Lindsey

Affiliation

¹ Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.

PMID: 16709082
DOI: 10.1021/jo060119b

Abstract

1-Formyldipyrromethanes are versatile precursors to porphyrins and chlorins. Two methods of synthesis of 1-formyldipyrromethanes have been investigated: (1) Vilsmeier formylation followed by selective removal of the unwanted 1,9-diformyldipyrromethane by dialkyltin complexation and (2) reaction with mesitylmagnesium bromide (MesMgBr) followed by formylation with phenyl formate. The two approaches are complementary (acidic versus basic conditions; statistical versus selective formylation). The latter was found to be more efficient for the preparation of 1-formyldipyrromethanes.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Hydrogen-Ion Concentration
Molecular Structure
Pyrroles / chemical synthesis*

Substances

Pyrroles

Grants and funding

GM-36238/GM/NIGMS NIH HHS/United States