Abstract:Zusammenf assung. Es wird eine neue Ringverengerungs-Methode fur D -Homosteroide beschrieben. Sie beruht auf der Beckmum'schen Umlagerung von or-Isonitrosoketonen und Cyclisierung der erhaltenen Nitrilcarbonsauren. Das Verfahren wird am Beispiel der Uberfuhrung des ds314-1,7-Dioxo-8,ll-dimethyl-dodecahydro-phenanthrens (I) ins 1-0x0-cyclopenta [4,5 a]d5210-6 -0x0 -2,5-dimethyl-octahydro-naphtalin(XII) naher erlautert.Forschungslaboratorien der CIBA Aktiengesellschuft, Base1Pharmazeutische Abteilung.
“…The first was prepared in a single step from the imide 10 as noted in Scheme , and the second, 8 , utilized the short sequence in the same scheme using a modified Reich procedure for introduction of the conjugation . Both synthetic reactants 10 and 11 were known. , 1 Synthesis of Two of the Photochemical Reactants…”
In contrast to the photochemistry of monocyclic aza-cyclohexenones, their counterparts with a second carbonyl group undergo photochemical rearrangements which parallel those of the 4,4-disubstituted cyclohexenones.
“…The first was prepared in a single step from the imide 10 as noted in Scheme , and the second, 8 , utilized the short sequence in the same scheme using a modified Reich procedure for introduction of the conjugation . Both synthetic reactants 10 and 11 were known. , 1 Synthesis of Two of the Photochemical Reactants…”
In contrast to the photochemistry of monocyclic aza-cyclohexenones, their counterparts with a second carbonyl group undergo photochemical rearrangements which parallel those of the 4,4-disubstituted cyclohexenones.
“…A mixture of 12 g (80.5 mmol) of 3,6-dichloropyridazine and 60 ml of an-hydrous diethylamine was heated in a stainless bomb at 150°for 4 hr. After cooling, the excess of base was evaporated; the residue was taken up with H20, filtered, and crystallized to give 5. Method D. 3-ChIoro-6-(3-dimethylaminopropoxy)pyridazine Hydrochloride (18). To 9.2 g (0.40 g-atom) of sodium in 140 ml of dry xylene, 45.5 g (0.44 mol) of 3-dimethylamino-l-propanol was slowly added and the mixture was heated to the reflux temperature until reaction was complete.…”
Section: Methodsmentioning
confidence: 99%
“…6-Alkoxy-3-hydrazinopyridazines (VI, Table V) were prepared by heating I in xylene with the appropriate sodium alkoxide (method D) to give III (X = 0), with the exception of 20 which was obtained by heating I with IV-(2hydroxyethy 1)aniline in anhydrous DMF in the presence of K2C03 (method E). These intermediates [17][18][19][20] (Table II) were then allowed to react with hydrazine to afford the products (method I).…”
3-Hydrazinopyridazines substituted in position 6 with a primary amine, secondary amine, or an alkoxy group were synthesized and screened for antihypertensive activity. In general, the 6-dialklamino derivatives are the most active; the (2-hydroxypropyl)methylamino chain provides the best combination of high antihypertensive activity and toxicity.
“…2-(p-Hydroxyphenyl)-2-ethylglutarimide (18). A solution of 700 mg (3.3 mmol) of 16 in 20 ml of 2 IV H2SO4 was cooled to 5°a nd diazotized with 480 mg (7 mmol) of NaN02 dissolved in 2 ml of H2O at 5°.…”
“…The aromatic-substituted glutethimide analogs were prepared according to previously reported procedures21 (Scheme III). 2-(p-Hydroxyphenyl)-2-ethylglutarimide (18) was prepared by diazotization of 16 followed by reflux in acidic medium.…”
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