ChemInform Abstract: UEBER DIE CYCLISIERUNG DER N‐ACETONYL‐ANTHRANILSAEURE

Zav’yalov, S. I.; Махова, Н. Н.; Aronova, N. I.; Mustafaeva, I. F.

doi:10.1002/chin.197215261

Cited by 1 publication

(3 citation statements)

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“…6-(Benzoyloxy)-3,4,5,6,7,8-hexahydro-2(lH)-quinolinone (21; R = ). A solution of 52 g (0.24 mol) of 4-(benzoyloxy)cyclohexanone (20),22 30 mL of pyrrolidine, and a few crystals of p-toluenesulfonic acid hydrate in 1000 mL of benzene was refluxed under a Dean-Stark water separator for 1 h. The benzene was distilled in vacuo, and the residue was dissolved in 1000 mL of dioxane. Acrylamide, 42.6 g (0.6 mol), was added, and the solution was heated under reflux under N2 for 21 h. The solvent was distilled under reduced pressure, and the crude product was chromatographed twice on Florisil using CHCl3/0-2% MeOH: yield 46.5 g (72%); mp 115-132 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Our plan in this case was to construct a suitable octahydro-6 (2H) -quinolinone (22) and then employ the above synthesis of Zav'yalov et al 20 to build on the requisite pyrrole ring. The first objective was accomplished using a standard quinoline synthesis21 by converting 4-(benzoyloxy) cyclohexanone (20)22 to its pyrrolidine enamine. AcC7/" 7 This on reaction with acrylamide gave the hexahydro-2-(lH)-quinolinone 21 (R = H).…”

mentioning

confidence: 99%

“…Chem., 17, 312 (1974). (20) with propylamine and ethyl a-(bromomethyl)acrylate gave the octahydroquinoline diester 28. This was converted to the enammonium salt, which with borohydride was reduced to the trans-decahydroquinoline 29.…”

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confidence: 99%

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Bicyclic and tricyclic ergoline partial structures. Rigid 3-(2-aminoethyl)pyrroles and 3- and 4-(2-aminoethyl)pyrazoles as dopamine agonists

Nj¹,

Ec²,

Nd³

et al. 1980

J. Med. Chem.

181

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It is proposed, based upon comparisons with apomorphine, that the rigid pyrroleethylamine moiety of the ergolines is the portion of the molecule responsible for dopamine agonist activity. In support of this hypothesis, bicyclic and tricyclic ergoline partial structures 6, 11, 25, and 35 have been synthesized. In addition, some pyrazole isosters (37, 38, 40, and 45) of these rigid pyrroleethylamines have been made. All of the classes show dopaminergic activity in prolactin inhibition and in lesioned rat turning assays. The most potent drugs, the linear tricyclic pyrazoles 38 (R = Pr) and 40 (R = Pr), are comparable in potency with the highly active ergoline pergolide (41).

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%