Title

Studies of spiro‐chlorin formation using porphyrin amides

Document Type

Article

Publication Date

1-1-1980

Abstract

Syntheses of 7‐(3‐ethoxycarbonylpropyl)‐2,3,5‐triethyl‐1,4,6,8‐tetramethylporphyrin (8) (via the MacDonald dipyrrylmethane route) and 2‐(2‐chloroethyl)‐4‐ethyl‐6‐methoxycarbonyl‐7‐(3‐methoxy‐carbonylpropyl)‐1,3,5,8‐tetramethylporphyrin (22) (via the tripyrrene route) are described. The corresponding pyrrolidides of these compounds were cyclized in high yield to furnish the spiro imines (20 and 30 respectively), but attempts to hydrolyze these imines to the appropriate spiroketochlorins were largely unsuccessful. A small amount of the spiroketochlorin 9 (from 8) was obtained, and this was successfully hydrogenated to give the dihydro derivative 21. The major problem in imine hydrolysis was observed to be reversion to the parent porphyrin through simple bond migration and spiro ring cleavage. A successful transformation of protoporphyrin‐IX dimethyl ester (31) into mesoporphyrin‐IX dimethyl ester (32) using di‐imide generated from dipotassium azodicarboxylate is described. Copyright © 1980 Journal of Heterocyclic Chemistry

Publication Source (Journal or Book title)

Journal of Heterocyclic Chemistry

First Page

481

Last Page

487

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