Studies on the stereochemistry of 1,2,6-trimethyl-4-piperidone

Diwischek, Florian; Arnone, Mario; Engels, Bernd; Holzgrabe, Ulrike

doi:10.1016/j.tet.2005.05.030

Cited by 12 publications

(9 citation statements)

References 23 publications

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“…33 1,2,6-Trimethyl-4-piperidone is an important intermediate in the synthesis of many drugs (opioid analgesics), which could be obtained starting from the DHA followed by catalytic hydrogenation and Swern oxidation. 34 The present study was focused on the design of CeO 2 -La 2 O 3 (CL) and CeO 2 -La 2 O 3 /SiO 2 (CLS) catalysts for the production of 4-methylpent-1-ene and DHA. The described 4-methylpent-1-ene and DHA products were synthesized by catalytic dehydration of 4-methylpentan-2-ol and self-condensation of ethyl acetoacetate, respectively.…”

Section: Introductionmentioning

confidence: 99%

Preparation of silica supported ceria–lanthana solid solutions useful for synthesis of 4-methylpent-1-ene and dehydroacetic acid

Katta

Sudarsanam

Mallesham

et al. 2012

Catal. Sci. Technol.

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The intriguing research toward the exploitation of ceria-based materials for various applications has been growing significantly. In the present investigation, we describe the preparation, characterization and utilization of CeO 2 -La 2 O 3 (CL) and CeO 2 -La 2 O 3 /SiO 2 (CLS) solid solutions for the synthesis of two industrially useful chemicals namely 4-methylpent-1-ene and dehydroacetic acid. Coprecipitation and deposition coprecipitation from ultrahigh dilute solutions were used for the synthesis of CL and CLS catalysts, respectively. The physicochemical characterization has been achieved with the help of various techniques namely X-ray diffraction (XRD), BET surface area, transmission electron microscopy (TEM), UV-visible diffuse reflectance spectroscopy (UV-vis DRS), Raman spectroscopy (UV-RS and Vis-RS), X-ray photoelectron spectroscopy (XPS) and temperature programmed desorption (TPD) measurements. The structure-activity relationships helped to correlate different parameters that are necessary for obtaining desired products in good yields. The inclusion of silica support has an optimistic influence on the acid-base properties of the ceria-lanthana, in terms of both amount and strength of sites. The presence of silica not only manipulates the acid-base properties but also causes numerous benefits, for instance, it improves the dispersion, stabilizes the active component against sintering and enriches the oxygen vacancy concentration. The meticulous analysis of characterization and activity studies revealed the significant role of acid-base sites in directing the desired products. Interestingly, the CLS catalyst has shown better performance in the production of both 4-methylpent-1-ene and dehydroacetic acid compared to the unsupported CL sample due to well-balanced acid-base sites.

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Section: Introductionmentioning

confidence: 99%

Preparation of silica supported ceria–lanthana solid solutions useful for synthesis of 4-methylpent-1-ene and dehydroacetic acid

Katta

Sudarsanam

Mallesham

et al. 2012

Catal. Sci. Technol.

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“…Thiazoles are the important group of heterocyclic compounds due to their drug utility [13]. In continuation of our earlier work some 2-(2-(3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinyl)benzo [d]thiazoles (11)(12)(13)(14) were synthesized in the present study and their conformational behaviour was analyzed using 1 H and 13 C NMR spectroscopy. The preferred conformations were further confirmed by means of conformational analysis performed by DFT calculations.…”

Section: Introductionmentioning

confidence: 88%

“…After cooling, the product was filtered and then washed with water. The products (11)(12)(13)(14) were purified by column chromatography. All the synthesized compounds were obtained in good yield and their analytical data are given in Table 1 and their synthetic methodology is given in Scheme 1 ( …”

Section: Synthesis Of 2-hydrazinobenzothiazole 10mentioning

confidence: 99%

“…Recently attention has been focused on the application of the piperidone derivatives as prospective biophotonic materials [9,10]. Since the pharmacological properties and the reactivity depend on their stereochemistry, efforts were made for the development of new synthetic techniques leading to stereoselective piperidines and their characterization [11,12]. Thiazoles are the important group of heterocyclic compounds due to their drug utility [13].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Spectral and Computational Studies of some 2-(2-(3-Methyl-2,4-Diphenyl-3-Azabicyclo[3.3.1]Nonan-9-Ylidene)Hydrazinyl)Benzo[d]Thiazole Derivatives

Sundararajan

Rajaraman

Bharanidharan

et al. 2015

ILCPA

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ABSTRACT. A series of some 2-(2-(3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinyl)benzo[d]thiazole derivatives 11-14 have been synthesized using acetic acid as the catalyst. All the synthesized compounds were characterized by FT-IR, 1 H 13 C NMR and HSQC spectral analysis. The molecular modelling was carried out for compound 11 by Gaussian 03W package and its HOMO-LUMO, Mulliken atomic charges, Molecular electrostatic potential (MEP), Hyperpolarizability, Thermodynamic propeties and Natural bond orbital (NBO) analysis were discussed.

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“…Recently, attention has been focussed on the application of the piperidone derivatives as prospective biophotonic materials (Nesterov et al, 2003;Sampathkumar et al, 2005). Since the pharmacological properties and the reactivity depend on their stereochemistry, efforts were made for the development of new synthetic techniques leading to stereoselective piperidines and their characterization (Garcia et al, 2004;Diwischek et al, 2005). Most of the piperidine precursors are known to exist in chair conformation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectral, theoretical, and antimicrobial screening of some heterocyclic oximes

2010

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In a wide research program toward new and efficient antimicrobial agents, a series of substituted N-nitroso-3-alkyl piperidone oximes were synthesized and their antibacterial activity against Staphylococcus aureus, Pseudomonas aerugonisa, Escherichia coli, and Klbesiella pneumoniae and antifungal activity against Aspergillus niger, Aspergillus flavus, and Rhizopus were evaluated. Their structure and stereochemistry were characterized by high-resolution 1 H NMR, mass and elemental analysis. The spectra of all N-nitroso oximes reveal the presence of two isomers labeled as E (-NOH group is anti to N-N=O moiety) and Z (-NOH group is syn to N-N=O moiety) in solution and the coupling constants ruled out the possibility of normal chair conformation. From the theoretical studies and coupling constant values, it was found that all N-nitroso oximes exist as an equilibrium mixture of CA boat conformation (B 1 ) and the major isomer was found to be E isomer. The molecular structure of N-nitroso oximes were also determined by semiempirical and Gaussian-03 calculation and the results are in agreement with the experimental studies.

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Studies on the stereochemistry of 1,2,6-trimethyl-4-piperidone

Cited by 12 publications

References 23 publications

Preparation of silica supported ceria–lanthana solid solutions useful for synthesis of 4-methylpent-1-ene and dehydroacetic acid

Preparation of silica supported ceria–lanthana solid solutions useful for synthesis of 4-methylpent-1-ene and dehydroacetic acid

Synthesis, Spectral and Computational Studies of some 2-(2-(3-Methyl-2,4-Diphenyl-3-Azabicyclo[3.3.1]Nonan-9-Ylidene)Hydrazinyl)Benzo[d]Thiazole Derivatives

Synthesis, spectral, theoretical, and antimicrobial screening of some heterocyclic oximes

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