Quinuclidine chemistry. I. Configuration and chemistry of 2-substituted benzylidene-3-quinuclidinones

Warawa, E. J.; Campbell, John R.

doi:10.1021/jo00938a014

Cited by 35 publications

(12 citation statements)

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“…Chemistry. 2-p-Fluorobenzylidene-3-quinuclidinone (1). A solution of 12.50 g (0.10 mol) of 3-quinuclidinone and 12.40 g (0.10 mol) of p-fluorobenzaldehyde in 25 ml of ethanol was treated with one pellet of sodium hydroxide, refluxed for 2.5 hr, and stirred overnight at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Quinuclidine chemistry. 2. Synthesis and antiinflammatory properties of 2-substituted benzhydryl-3-quinuclidinols

Warawa¹,

Mueller²,

Jules³

1974

J. Med. Chem.

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Section: Methodsmentioning

confidence: 99%

Quinuclidine chemistry. 2. Synthesis and antiinflammatory properties of 2-substituted benzhydryl-3-quinuclidinols

Warawa¹,

Mueller²,

Jules³

1974

J. Med. Chem.

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“…Conversion of the (Z) isomers into an equilibrium mixture of (Z) and (E) isomers was previously performed in HCl-saturated chloroform [18]. Under these conditions, 2-hydroxyketone Ib is virtually completely (TLC) converted into a cyclic semiketal, chromeno [3,2-b]quinuclidine HI.…”

mentioning

confidence: 99%

Search for no donors. Part I. 3-Quinuclidone oximes

Koikov¹,

Алексеева²,

Grigor'ev³

et al. 1997

Pharm Chem J

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Identification of the "endothelial relaxation factor" as the endogenic NO formed from L-arginine in the vascular endothelium [1] has stimulated the search for new generation of cardiovascular drugs [2][3][4][5]. At present, it has been established that biochemical synthesis of NO proceeds by different pathways. Exogenic organic nitrates (nitroglycerin, nitrosorbid, and other classical vasodilators) are subject to reduction [6], as well as the new NO precursors such as N-nitropyrazoles [7] and furoxanes [8]. On the contrary, L-arginine -the main NO source in the organism -is oxidized by the enzyme NO-synthase (NOS) to . NOS is also capable of forming NO from [3-mercaptoethylguanidine [9,10]. Study of the weU-known vasodilator molsidomin showed that this agent generates NO by reaction with atmospheric oxygen [3]. It was found that 1,2-diazetine-l,2-dioxides form NO upon thermolysis and/or hydrolysis [I1]. Muller et al. [12] reported on the use of (+)-3-(E)-4ethyl-2[(E)-hydroxyimino]-5-nitro-3-hexenamide (FK 409) as the NO donor in solutions at pH -7.5, but failed t o establish a group (oxime, nitro, or both) acting as the source of NO [12]. Recently we have demonstrated that 3-quinuclidone oximes may serve as the source of NO and activate the soluble guanylate cyclase [13]. The purpose of this work was to extend the group of oximes and study their hypotensive activity.The NO precursors were obtained on the basis of both well-known (Va/VIa, Vb/VIb, Ve/VIe, Vi/VIi) [14], (Vc/VIc, Vd/VId, VIIb] [13], and newly synthesized (VfiVlfVh/VIh) 2-arylmethylene-3-quinuclidone oximes and their hydrogenated analogs IXb and IXe. The compact rind framework structure of quinuclidine (1-azabicyclo[2.2.2]octane) provides spatial fixation of the substituents and sufficiently high solubility of hydrochlorides, while the double bond in position 2 sometimes allows us to obtain the (Z/E) isomer

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“…The formation of the dications 158 was confirmed by NMR spectroscopy. 299,307 Under the action of gaseous HCl in chloroform 288,290,295,308 or of NaBPh 4 in acetic acid, 299,307 the compounds 151 underwent reversible Z,E isomerisation. For example, Z-2-arylmethylideneand Z-2-ferrocenylmethylidenequinuclidinones are readily (often quantitatively in a matter of minutes) transformed into the corresponding E isomers.…”

Section: Methylidene-and Arylmethylidenequinuclidin-3-onesmentioning

confidence: 99%

“…When subjected to platinum-or palladium-catalysed hydrogenation, methylidene-and arylmethylidenequinuclidinones were transformed into saturated ketones 173. 288,291,292,298,305 The corresponding allylic alcohols 174 were selectively obtained with the use of NaBH 4 . 288,308,324,325 Stereospecific reduction of both functional groups in the benzylidenequinuclidinone 151 (R = Ph) with lithium aluminium hydride afforded benzylquinuclidinol trans-175 (R = Ph).…”

Section: Methylidene-and Arylmethylidenequinuclidin-3-onesmentioning

confidence: 99%

“…288,291,292,298,305 The corresponding allylic alcohols 174 were selectively obtained with the use of NaBH 4 . 288,308,324,325 Stereospecific reduction of both functional groups in the benzylidenequinuclidinone 151 (R = Ph) with lithium aluminium hydride afforded benzylquinuclidinol trans-175 (R = Ph). 326 Catalytic hydrogenation of the same compound 151 (R = Ph) followed by reduction with NaBH 4 gave rise to cis-175 (R = Ph).…”

Section: Methylidene-and Arylmethylidenequinuclidin-3-onesmentioning

confidence: 99%

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