Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate

Kostyanovsky, Remir G.; El’natanov, Yurii I.; Червин, И. И.; Коновалихин, С. В.; Zolotoi, A. B.; Atovmyan, L. O.

doi:10.1070/mc1996v006n04abeh000619

Cited by 8 publications

(4 citation statements)

References 7 publications

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“…To understand this behaviour, we have examined the geometric parameters selected in the first part of this work for the following two entries: KOWRIX 37 (I) and TIZMEU 38 (II) (the HBA investigated in this study and the HBD groups involved are indicated in bold).…”

Section: Fragments With Hb To O Carbonyl Cmentioning

confidence: 99%

Amino nitrogen and carbonyl oxygen in competitive situations: which is the best hydrogen-bond acceptor site?

2002

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Section: Fragments With Hb To O Carbonyl Cmentioning

confidence: 99%

Amino nitrogen and carbonyl oxygen in competitive situations: which is the best hydrogen-bond acceptor site?

2002

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“…The proposed scheme is supported by specific transformation of 2,2,6,6-tetramethylpiperidin-4-one in the reaction with dimethyl acetylenedicarboxylate, which led to the formation of the corresponding N-maleate and/or dimethyl 4-hydroxy-2,3-dehydroquinuclidine-2,3-dicarboxylate derivative [2][3][4].…”

Section: Schwan and Warkentinmentioning

confidence: 94%

Unexpected cascade synthesis of 1-azabicyclo[3.3.1]nonanes by nucleophilic reaction of bis(2-aroylethyl)methanamines with dimethyl acetylenedicarboxylate

et al. 2015

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SHORT COMMUNICATIONS Schwan and Warkentin [1] previously synthesized 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridin-4-ol in one step by reaction of 3-(dimethylamino)-1-phenylpropan-1-one with dimethyl acetylenedicarboxylate. We have studied the reaction of dimethyl acetylenedicarboxylate with 3,3′-(methylimino)bis(1-phenylpropan-1-one) (1) and 3,3′-(methylimino)bis[1-(thiophen-2-yl)propan-1-one] (2). Tertiary amines 1 and 2 each possess two reactive carbonyl groups in the β-position with respect to the nitrogen atom, which makes it difficult to predict the reaction direction.We have found that the reactions of 1 and 2 with dimethyl acetylenedicarboxylate involve a sequence of transformations eventually leading to double cyclization products 3 and 4, respectively, which have the structure of polysubstituted azabicyclo[3.3.1]nonanes. Presumably, the cascade process begins with attack by amine 1 or 2 on the activated triple bond of dimethyl 1, 3, R = Ph; 2, 4, R = thiophen-2-yl.

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“…The racemic crystal of compound 1 consists of enantiomeric pairs of diastreomers with the relative configuration of the chiral centers rac-4S*,4аS*,8аS*. In the study of chemical modification of compound 1 by the reaction with acetylenecarboxylic ester (aiming at its N-demethylation [9,10], N-vinylation [10,11], and cyclization at the carbonyl carbon atom [10][11][12][13]) we discovered a quite unexpected transformation of the piperidine ring in an eight-membered cycle with the formation of compound 2 isolated by chromatography in 23% yield. The structure of compound 2 was confirmed by spectral data.…”

Section: Methodsmentioning

confidence: 99%

Uncommon expansion of piperidine ring into hydroazocine ring in reactions of some piperidine β-acyl derivatives with acetylenecarboxylic acids esters

et al. 2016

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Cyclohexanone condensation with formaldehyde and methylamine led to the formation of 4ahydroxy-2-methyloctahydrospiro[isoquinoline-4,1'-cyclohexan]-2'-one whose structure was established by means of X-ray diffraction (XRD) analysis. This spiro compound reacted with acetylenecarboxylic acids esters with unexpected conversion of its piperidine ring into a hexahydroazocine cycle. The uncommon expansion reaction of the β-acyl-substituted piperidine ring into a hexahydroazocine cycle is confirmed by the analogous conversion of 4-hydroxy-1-methyl-4-phenylpiperidin-3-yl(phenyl)methanone into azocine derivative at treating with methyl propiolate.

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Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ2-dehydroquinuclidine-2,3-di-carboxylate

Cited by 8 publications

References 7 publications

Amino nitrogen and carbonyl oxygen in competitive situations: which is the best hydrogen-bond acceptor site?

Amino nitrogen and carbonyl oxygen in competitive situations: which is the best hydrogen-bond acceptor site?

Unexpected cascade synthesis of 1-azabicyclo[3.3.1]nonanes by nucleophilic reaction of bis(2-aroylethyl)methanamines with dimethyl acetylenedicarboxylate

Uncommon expansion of piperidine ring into hydroazocine ring in reactions of some piperidine β-acyl derivatives with acetylenecarboxylic acids esters

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