ChemInform Abstract: The Chemistry of Pyrrolic Compounds. Part 64. Intramolecular Cyclization of Butyric Acid-Substituted Porphyrins: Petroporphyrins with Fused Seven-Membered Ring Systems.

P. S. CLEZY; U. JENIE; J. K. PRASHAR

doi:10.1002/chin.199036228

ChemInform Abstract: The Chemistry of Pyrrolic Compounds. Part 64. Intramolecular Cyclization of Butyric Acid-Substituted Porphyrins: Petroporphyrins with Fused Seven-Membered Ring Systems.

ChemInform ◽

10.1002/chin.199036228 ◽

1990 ◽

Vol 21 (36) ◽

Author(s):

P. S. CLEZY ◽

U. JENIE ◽

J. K. PRASHAR

Keyword(s):

Intramolecular Cyclization ◽

Butyric Acid ◽

Membered Ring ◽

Ring Systems

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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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Studies on double acylation of aromatic hydrocarbons. XI. A total synthesis of 5,6-Dihydro-4H-benz[de]anthracene

Australian Journal of Chemistry ◽

10.1071/ch9721521 ◽

1972 ◽

Vol 25 (7) ◽

pp. 1521 ◽

Cited By ~ 1

Author(s):

A Rahman ◽

BM Vuano ◽

NM Rodriguez

Keyword(s):

Total Synthesis ◽

Propionic Acid ◽

Intramolecular Cyclization ◽

Butyric Acid ◽

Aromatic Hydrocarbons ◽

Dibasic Acid ◽

Membered Ring ◽

Ring Closure ◽

Partial Synthesis

Starting from ethyl 3-(1-naphthyl)propionate (1), the dibasic acid 4-(4-carboxy-ethyl-I-naphthyl)butyric acid (3) was prepared, which served as a key compound for the synthesis of 5,6-dihydro-4H-benz[de]anthraoene (6) by a double intramolecular cyclization. The monocyolization of the dibasic acid (3) gave rise by a preferential six-membered ring closure, to 3-(1-oxo-1,2,3,4-tetrahydro-9-phenanthryl)propionic acid (7). A partial synthesis of 5,6-dihydro-4H-benz[de]anthracene (6), by succinoylation of perinaphthane followed by usual synthetic steps, is reported as confirmatory evidence of the identity of (6) obtained by double cyclization of the diacid. Some aspects of the orientation of intramolecular acylation are discussed.

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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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