Seven-membered Ring Compounds. IX. Benzosuberoneglyoxylates

Anderson, Charles L.; Horton, W. J.; Walker, F. E.; Weiler, M.

doi:10.1021/ja01608a023

Cited by 9 publications

(1 citation statement)

References 2 publications

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“…Into 300 mL of methanol containing 100 mL of water and 0.5 mL of 70% perchloric acid was dissolved 11.4 g (0.045 mol) of 5-(2,5-dimethoxyphenyl)-5-ketopentanoic acid. 24 The solution was hydrogenated over 1 g of 10% Pd/C at 60 °C and 50 psi for 8 h. The mixture was filtered through Celite, and the filtrate was treated with 50 mL of 10% NaOH and refluxed for 4 h. The methanol was removed under vacuum, and the aqueous phase was extracted with EtjO, which was discarded. The solution was acidified with 3 N HC1 and extracted with EtjO.…”

Section: Demarinis Et Almentioning

confidence: 99%

.alpha.-Adrenergic agents. 1. Direct-acting .alpha.1 agonists related to methoxamine

DeMarinis¹,

Bryan²,

Shah³

et al. 1981

J. Med. Chem.

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A series of phenylethylamines related to methoxamine has been prepared and evaluated for direct alpha 1-receptor agonist activity. It has been observed that for open-chain compounds such as methoxamine, in which the amine-containing portion is free to adopt numerous conformations, an hydroxyl group is necessary for direct alpha 1-adrenergic activity. When the hydroxyl is removed, however, the direct component of activity is greatly reduced unless the amine is incorporated into a more sterically defined structure. From our studies we have concluded that in order for a phenylethylamine to be active as a direct alpha 1-receptor agonist it should have a beta nitrogen in a fully extended conformation relative to a substituted phenyl ring. For optimum potency, the nitrogen should be exocyclic to a saturated six-membered ring. It may be further incorporated exocyclic or endocyclic into an additional ring as long as the amine occupies a well-defined region of space relative to the aromatic portion of a molecule. The ED50 values of some of the more potent compounds as alpha 1-receptor agonists are on the order of 1 X 10(-7) M.

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Section: Demarinis Et Almentioning

confidence: 99%

.alpha.-Adrenergic agents. 1. Direct-acting .alpha.1 agonists related to methoxamine

DeMarinis¹,

Bryan²,

Shah³

et al. 1981

J. Med. Chem.

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Furan derivatives. Part 9. Synthesis and properties of cyclohepta[cd]benzofurans

Horaguchi¹,

Toko²,

Suzuki³

1988

Journal of Heterocyclic Chem

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Cyclohepta[cd]benzofurans 1a‐c were synthesized by heating (5‐oxo‐5H‐benzocyclohepten‐4‐yloxy)acetic acids 7a‐c with sodium acetate in acetic anhydride or by irradiation of 7a‐c in acetonitrile. Several reactions such as protonation, catalytic hydrogenation, Diels‐Alder reaction, acylation, and photoreaction were examined for 1a‐b. The results show that cyclohepta[cd]benzofurans have both properties of heptafulvene and benzofuran. The carbon‐carbon double bond in the furan ring of 1a has aromatic character, however, the carbon‐carbon double bonds in the seven‐membered ring have olefinic character.

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Furan derivatives. Part 10. Synthesis of cyclohepta[cd]benzofuran

Horaguchi

Hasegawa

Shimizu

et al. 1989

Journal of Heterocyclic Chem

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Cyclohepta[cd]benzofuran 2 was synthesized by heating (5‐oxo‐5H‐benzocyclohepten‐4‐yloxy)acetic acid 16 with sodium acetate in acetic anhydride or by photocyclization of 16 in acetonitrile. Several reactions of cyclohepta[cd]benzofuran 2 were examined. Protonation of 2 with trifluoroacetic acid occurred at the 2‐position to give a tropylium ion 17. Catalytic hydrogenation of 2 with palladium on charcoal proceeded smoothly to give tetrahydrocyclohepta[cd]benzofuran 18. The Diels‐Alder reaction of 2 with tetracyano‐ethylene produced an adduct 19. Formylation of 2 with phosphorus oxychloride and dimethylformamide occurred easily at the 2‐position to afford compound 20. Cyclohepta[cd]benzofuran 2 has both properties of heptafulvene and benzofuran.

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Seven-membered Ring Compounds. IX. Benzosuberoneglyoxylates

Abstract: amount of benzoyl peroxide were mixed and the solution allowed to reflux for four hours as its temperature increased from 75 to 190°. The material was then distilled, and the 71 g. of distillate collected up to 190°at 50 mm. was frac-

Cited by 9 publications

References 2 publications

.alpha.-Adrenergic agents. 1. Direct-acting .alpha.1 agonists related to methoxamine

.alpha.-Adrenergic agents. 1. Direct-acting .alpha.1 agonists related to methoxamine

Furan derivatives. Part 9. Synthesis and properties of cyclohepta[cd]benzofurans

Furan derivatives. Part 10. Synthesis of cyclohepta[cd]benzofuran

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