The Chemistry of Pyrrolic Compounds. LXIII. Synthetic Studies of Petroporphyrins With Fused Six-Membered Ring Systems

PS Clezy; JK Prashar

doi:10.1071/ch9900825

The Chemistry of Pyrrolic Compounds. LXIII. Synthetic Studies of Petroporphyrins With Fused Six-Membered Ring Systems

Australian Journal of Chemistry ◽

10.1071/ch9900825 ◽

1990 ◽

Vol 43 (5) ◽

pp. 825 ◽

Cited By ~ 12

Author(s):

PS Clezy ◽

JK Prashar

Keyword(s):

Intramolecular Cyclization ◽

Membered Ring ◽

Stannic Chloride ◽

Side Chain ◽

Ring Systems ◽

Synthetic Studies

Several approaches to the synthesis of porphyrins bearing fused six- membered ring systems were explored with the aim of obtaining the petroporphyrin (4a). This was ultimately achieved by an intramolecular cyclization of a porphyrin with a propanoyl chloride side chain in the presence of stannic chloride. Methylation of the intermediate ketone with CH3Li and reduction of the resultant alcohol with NaBH3CN/Znl2 furnished (4a).

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ChemInform Abstract: Synthetic Studies of Pyridomycin. Part 4. Syntheses of Some Twelve-membered Ring Compounds Designed for Construction of Intact Ring System with Exocyclic (Z)-s- Butylidene Side Chain in Pyridomycin.

Chemischer Informationsdienst ◽

10.1002/chin.198610375 ◽

1986 ◽

Vol 17 (10) ◽

Author(s):

M. KINOSHITA ◽

Y. MORI

Keyword(s):

Ring System ◽

Membered Ring ◽

Side Chain ◽

Ring Compounds ◽

Synthetic Studies

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The Chemistry of Pyrrolic Compounds. LXIV. Intramolecular Cyclization of Butyric Acid Substituted Porphyrins: Petroporphyrins With Fused Seven-Membered Ring Systems

Australian Journal of Chemistry ◽

10.1071/ch9900839 ◽

1990 ◽

Vol 43 (5) ◽

pp. 839 ◽

Cited By ~ 8

Author(s):

PS Clezy ◽

U Jenie ◽

JK Prashar

Keyword(s):

Intramolecular Cyclization ◽

Butyric Acid ◽

Membered Ring ◽

Side Chains ◽

Ring Systems ◽

Porphyrin Macrocycle

The preparation of a series of porphyrins substituted with butyric acid side chains is described and efforts to achieve the intramolecular cyclization of this substituent are discussed. Attempts to prepare a stable spiro ketone by cyclization onto a β- pyrrolic carbon have not met with success but the synthesis of a seven- membered ring ketone by cyclization onto a meso -carbon has been completed. Reduction of this ketone has led to the synthesis of the petroporphyrin (1d). Some comments are offered concerning the origin of the isomeric petroporphyrin (19a) which bears a methylated six- membered ring sytem fused to the porphyrin macrocycle.

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