Tetrahedron

Porphyrins with exocyclic rings. Part 5. Synthesis of a naphtho [1, 2-b] porphyrin.

TD Lash, CP Denny

Index: Lash, Timothy D.; Denny, Carl P. Tetrahedron, 1995 , vol. 51, # 1 p. 59 - 66

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Citation Number: 46

Abstract

Condensation of 2-acetyl-1-tetralone with diethyl aminomalonate in refluxing acetic acid gave a dihydronaphtho-pyrrole 9a in excellent yield. Transesterification with benzyl alcohol gave the corresponding benzyl ester 9b and subsequent regioselective oxidation with lead tetraacetate afforded the acetoxymethyl derivative 13. Pyrrole 13 condensed with the α- unsubstituted pyrrole 14 to give the asymmetrical dipyrrylmethane 15 and hydrogenolysis ...