L. N. Koikov

Acetyl Derivatives of 3-Quinuclidone

Methods have been developed for the synthesis of mono- and bisacetyl derivatives of 2-hydroxyarylmethylene-3-quinuclidone oximes.

7-Aryl-4a-hydroxy-4a,6,7,7a-tetrahydroisoxazolo[4,5-b]quinuclidines as NO Donors

Abstract7-Aryl-4a-hydroxy-4a,6,7,7a-tetrahydroisoxazolo[4,5-b]quinuclidines have been prepared from 2-arylmethylene-3-quinuclidones and hydroxylamine and they are able to release NO upon mild oxidation with K3[Fe(CN6)] in basic medium.

Thiophene monolithiumization with phenyllithium as a key stage in the large-scale synthesis of Di(2-thienyl)(3-quinuclidyl)carbinol—The new potential antiulcerous drug quiditene

The results of extensive investigations devoted to the synthesis and properties of quinuclidine compounds, conducted at the Center for Drug Chemistry (Moscow) [ 1 5], showed that di(2-thienyl)(3-qninuclidyl)carbinol hydrochloride (It), a thiophene analog of the antiallergic drugs phencarol (Ia) and bicarphen (Ib), possesses pronounced antisecretor and antiulcerous activity [6]. The previous publication [7] reported on a method developed for the synthesis of compound Ic, called quiditene, proceeding from 2-thienyllithium (II) and 3-ethoxyearbonylquinuclidine (IV):

Condensation of N-ethylpiperid-4-one with benzaldehyde

Reaction of N-ethylpiperid-4-one with benzaldehyde and KOH in 65% aqueous methanol gives 2,7-diethyl-10a-hydroxy-9-phenyl-4-(phenylmethylene)-2,7-diaza-10-oxa-1,2,3,4,5,6,7,8,8a, 10a-decahydroanthracene. In the presence of HCl/EtOH, 3,5-bis(phenylmethylene)-1-ethylpiperid-4-one is formed. In the presence of HCl/AcOH, 2,7-diethyl-9-phenyl-4,5-bis(phenylmethylene)-2,7-diaza-10-oxa-1,2,3,4,5,6,7,8-octahydroanthracene is formed.

Purification of 3-ethoxycarbonylquinuclidine and its conversion to 3-quinuclidinecarboxylic acid and 3-quinuclidinylmethanol

Abstract3-Ethoxycarbonylquinuclidine obtained by the Grob method is a mixture of 3-ethoxycarbonyl-1-azabicylo-[2.2.2]- and, according to 13C NMR data, 5-ethoxycarbonyl-5-azatricyclo[3.2.1.02,7]octanes (∼16∶2∶1). 3-Ethoxy-carbonylquinuclidine was purified by recrystallization of the hydrochloride, hydrolyzed by water to 3-quinuclidinecarboxylic acid, and reduced by LiAlH4 to 3-quinuclidinylmethanol.