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Synthesis of heterocycle-substituted pyropheophorbide derivatives

✍ Scribed by Jin-Jun Wang; Young Key Shim; Gui-Ji Jiang; Kimiaki Imafuku

Book ID
102341917
Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
64 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Methyl pyropheophorbide‐a (MPPa) (1) was converted to two aldehydes, methyl 2‐formylmethyl‐2‐devinylpyropheophorbide‐a (2) and methyl 2‐formyl‐2‐devinylpyropheophorbide‐a (3). The former 2 reacted with active methylene compounds having a cyano function in the presence of sulfur to afford thiophene‐substituted chlorins 5a‐c and reacted with arylhydrazines to yield indole‐substituted chlorins 6a‐d. From the latter 3, a α‐diketo chlorin 7 was obtained via Wittig reaction and oxidation. Compound 7 reacted with o‐phenylenediamine to afford 2‐quinoxalyl‐substituted pyropheophorbide‐a 8. The reaction of MPPa (1) with anthranilamide to give a spiro‐substituted compound 9.

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