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Synfacts 2006(4): 0341-0341
DOI: 10.1055/s-2006-932057
DOI: 10.1055/s-2006-932057
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York
Boron-Templated Synthesis of Subporphyrins
Y. Inokuma, J. H. Kwon, T. K. Ahn, M.-C. Yoo, D. Kim*, A. Osuka*
Yonsei University, Korea and Kyoto University, Japan
Further Information
Publication History
Publication Date:
24 March 2006 (online)
Significance
The first reported synthesis of subporphyrins is described. Condensing 2,3-dihydro-3-oxo-1H-isoindole-1-acetic acid with boric acid at high temperature produced a complex mixture. Repeated column chromatography provided the tribenzosubporphine in 1.4% overall yield. Tetrabenzoporphines are synthesized via zinc-templated condensation; the authors predicted that replacing the zinc with boron could produce the ring-contracted congener. The aromatic, C 3-symmetric tribenzosubporphine is an orange solid with a bowl-shaped structure and intense green fluorescence (517 nm).