Circular dichroism of heterocyclohexan-4-onic systems—II

Kashman, Yoel; Cherkez, S.

doi:10.1016/0040-4020(72)80064-4

Cited by 17 publications

(4 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Knowing that in tropinone the axial α-protons are deshielded versus the equatorial protons by ca. 0.5 ppm [12,25], we were also able to identify positively, within the pairs of interconverting isomeric TBDMS ethers, the isomer with exo and endo side chain (equatorial and axial α-CH, respectively). On the basis of the observed exo – endo isomerization, and trends in NMR data changes upon isomerization, we were fairly certain of the assigned stereochemistry of the new isomer as exo , syn - 3 .…”

Section: Resultsmentioning

confidence: 95%

Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

Łaźny¹,

Nodzewska²,

Sidorowicz³

et al. 2012

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe relative configurations of tert-butyldimethylsilyl (TBDMS) ethers of all four diastereomers of the aldols of tropinone (8-methyl-8-azabicyclo[3.2.1]octan-3-one), as well as of granatanone (9-methyl-9-azabicyclo[3.3.1]nonan-3-one), were determined from NMR data, and from the observed interconversion of the diastereomers (exo,anti to endo,syn and exo,syn to endo,anti). The exo forms invert to endo isomers in the presence of silica gel. The relative configuration of a new isomer of tropinone aldol accessible synthetically through the direct solventless reaction of tropinone and benzaldehyde in the presence of water was determined as exo,syn by comparison of NMR data of the aldol isomers, in particular vicinal coupling constants and shifts corresponding to the side-chain CH group, with data of related TBDMS derivatives and confirmed by single-crystal X-ray diffraction.

show abstract

Section: Resultsmentioning

confidence: 95%

Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

Łaźny¹,

Nodzewska²,

Sidorowicz³

et al. 2012

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Commercial MeNO 2 (Aldrich HPLC) was used as solvent without further purification. 9-( p -Anisyl)-9-azabicyclo[3.3.1]nonane ( 1d ) was obtained by reaction of cycloocta-2,6-diene with p -anisidine followed by Wolff−Kishner (W−K)reduction of the resulting 9- p -anisyl-9-azabicyclo[3.3.1]nonan-3-one. For both the steps, procedures were used that are described in the literature for analogous compounds. , By W−K reduction of 9.4 g of the azabicyclononanone, 1d was obtained along with the corresponding hydrolysis product, 9-(4-hydroxyphenyl)-9-azabicyclo[3.3.1]nonane.…”

Section: Methodsmentioning

confidence: 99%

Direct Evidence on Nucleophilic Reactivity of Secondary Anilines toward an Aminium Radical

Ciminale

2001

J. Org. Chem.

View full text Add to dashboard Cite

“…The nortropanones 6 can be prepared either from cyclohepta-2,6-dien-l-one [8] and the corresponding anilines 5 [9], or, more efficiently, by a…”

Section: Synthesis Of 2 and -mentioning

confidence: 99%

“…The monomethoxy derivatives were synthesized in an anulogous manner. Compound 6a was prepared according to a published procedure [9]. Usual workup means: The reaction mixture is diluted with the solvent indicated.…”

Section: Experimental Partmentioning

confidence: 99%

5‐(N‐Arylnortropan‐3‐yl)‐ and 5‐(N‐Arylpiperidin‐4‐yl)‐2,4‐diaminopyrimidines. Novel Inhibitors of Dihydrofolate Reductase

Maag

Locher

Daly

et al. 1986

Helvetica Chimica Acta

View full text Add to dashboard Cite

Based on a computer-assisted analysis of the three-dimensional structure of the binary complex of E. coli dihydrofolate reductase (DHFR) with methotrexate, S-(N-arylnortropan-3-y1)-and 5-(N-arylpiperidin-4-y1)-2,4diaminopyrimidines 2 and 4 were designed as inhibitors of DHFR. Syntheses of the designed compounds have been carried out. The most potent compound 2a inhibited E. coli DHFR with K, = 0.49. IO-'M. The activities within the series of compounds synthesized could be rationalized by molecular-modelling experiments which served as the basis of this work. Several compounds within the presented series exhibit antimalarial activities in vitro and in vivo.

show abstract

Circular dichroism of heterocyclohexan-4-onic systems—II

Cited by 17 publications

References 14 publications

Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

Direct Evidence on Nucleophilic Reactivity of Secondary Anilines toward an Aminium Radical

5‐(N‐Arylnortropan‐3‐yl)‐ and 5‐(N‐Arylpiperidin‐4‐yl)‐2,4‐diaminopyrimidines. Novel Inhibitors of Dihydrofolate Reductase

Contact Info

Product

Resources

About