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Journal articles on the topic 'N-alkyl piperidine'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Matulevičiūtė, Gita, Eglė Arbačiauskienė, Neringa Kleizienė, et al. "Synthesis and Characterization of Novel Methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates." Molecules 26, no. 13 (2021): 3808. http://dx.doi.org/10.3390/molecules26133808.

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Series of methyl 3- and 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates were developed and regioselectively synthesized as novel heterocyclic amino acids in their N-Boc protected ester form for achiral and chiral building blocks. In the first stage of the synthesis, piperidine-4-carboxylic and (R)- and (S)-piperidine-3-carboxylic acids were converted to the corresponding β-keto esters, which were then treated with N,N-dimethylformamide dimethyl acetal. The subsequent reaction of β-enamine diketones with various N-mono-substituted hydrazines afforded the target 5-(N-Boc-piperidinyl)-1H-pyrazol

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2

Silgado-Gómez, Kheila N., та Vladimir V. Kouznetsov. "Thermal aromatic Claisen rearrangement and Strecker reaction of alkyl(allyl)-aryl ethers under green reaction conditions: Efficient and clean preparation of ortho-allyl phenols (naphthols) and alkyl(allyl)oxyarene-based γ-amino nitriles". Mediterranean Journal of Chemistry 6, № 6 (2017): 208–14. http://dx.doi.org/10.13171/mjc65/01711201245-kouznetsov.

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Chemical transformations of 13 diverse allyl(alkyl)-aryl ethers, easily prepared using Williamson reaction of different hydroxyarenes and allyl bromide and alkyl (n-butyl, n-octyl) bromides, were studied. Thermal aromatic Claisen rearrangement of allyl-aryl ethers to obtain ortho-allyl phenols (naphthols) employing propylene carbonate as a nontoxic and biodegradable solvent was described for the first time. The use of this green solvent allowed to enhance notably product yields and reduce significantly the reaction time comparing with the use of 1,2-dichlorobenzene, toxic solvent, which is tra

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3

Sánchez García, Jessica J., Marcos Flores-Alamo, Mark E. Martínez Klimov, and Elena I. Klimova. "N-alkyl-2-(1,2-diferrocenylvinyl)-4,5-dihydrooxazolinium salts, multi-component synthesis and breaking of their heterocyclic systems." Pure and Applied Chemistry 88, no. 12 (2016): 1129–42. http://dx.doi.org/10.1515/pac-2016-0812.

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AbstractA new multicomponent method for the synthesis of N-alkyl-2-(Z-1,2-diferrocenylvinyl)-4,5-dihydrooxazolinium salts 3a–f, 5-(N-alkyl-2′,3′-diferrocenyl-acryloylamido)-3-aza-3-alkylpentanols 4a–d, (E)-N-alkyl-N-(2-morpholinoethyl)-2,3-diferrocenylacrylamides 9a,b,e,f and (E)-N-alkyl-N-(2-piperidinoethyl)-2,3-diferrocenylacrylamides 10a,c from reactions of 2,3-diferrocenylcyclopropenone 1 with bis-1,4-N,O-nucleophiles in the presence of triethyloxonium tetrafluoroborate, alkyl iodides, morpholine, piperidine and Et3N is described. The characterization of the new compounds was done by IR, 1

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4

Zamoner, Luís O. B., Valquiria Aragão-Leoneti, and Ivone Carvalho. "Iminosugars: Effects of Stereochemistry, Ring Size, and N-Substituents on Glucosidase Activities." Pharmaceuticals 12, no. 3 (2019): 108. http://dx.doi.org/10.3390/ph12030108.

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N-substituted iminosugar analogues are potent inhibitors of glucosidases and glycosyltransferases with broad therapeutic applications, such as treatment of diabetes and Gaucher disease, immunosuppressive activities, and antibacterial and antiviral effects against HIV, HPV, hepatitis C, bovine diarrhea (BVDV), Ebola (EBOV) and Marburg viruses (MARV), influenza, Zika, and dengue virus. Based on our previous work on functionalized isomeric 1,5-dideoxy-1,5-imino-D-gulitol (L-gulo-piperidines, with inverted configuration at C-2 and C-5 in respect to glucose or deoxynojirimycin (DNJ)) and 1,6-dideox

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5

Berardi, Francesco, Giuseppe Giudice, Roberto Perrone, Vincenzo Tortorella, Stefano Govoni та Laura Lucchi. "Novel Potent σ1Ligands: N-[ω-(Tetralin-1-yl)alkyl]piperidine Derivatives". Journal of Medicinal Chemistry 39, № 21 (1996): 4255–60. http://dx.doi.org/10.1021/jm9508898.

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6

Cote, Everett, Laura Chafin, Mike DiFazio, et al. "Development of a Scalable Synthesis of Oligomeric Piperidine-N-O-alkyl Ethers." Organic Process Research & Development 18, no. 12 (2014): 1843–49. http://dx.doi.org/10.1021/op500301r.

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7

Pabel, Jörg, Elmar Wadenstorfer, and Klaus T. Wanner. "Asymmetric Synthesis of Pyrido[1,2-c]pyrimidinones." Zeitschrift für Naturforschung B 64, no. 6 (2009): 653–61. http://dx.doi.org/10.1515/znb-2009-0610.

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“Asymmetric Electrophilic α-Amidoalkylation” reactions with a chiral alkylaminocarbonyl unit as chiral auxiliary are used for the stereoselective synthesis of 2-substituted piperidine derivatives. Intramolecular condensation of the nitrogen of the aminocarbonyl group with the keto function present in the newly introduced side chain of the amidoalkylation products results in the formation of hexahydropyrido[1,2-c]pyrimidinones. After reduction and removal of the N-alkyl moiety of the chiral auxiliary the target compounds, enantiopure octahydro-1H-pyrido[1,2-c]pyrimidin-1-ones, are obtained.

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8

Maeda, Satoshi, Tomoyo Mohri, Tsubasa Inoue, et al. "Synthesis of a plasmenylethanolamine." Bioscience, Biotechnology, and Biochemistry 85, no. 6 (2021): 1383–89. http://dx.doi.org/10.1093/bbb/zbab037.

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ABSTRACT A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through 8 steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are (1) regio- and Z-selective vinyl ether formation via the alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification–oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine s

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9

Ilamparithi, A., S. Ponnuswamy, and A. Selvaraj. "Inhibitive Effects of cis-2,6-Diphenyl-3-alkyl Piperidine at Aluminium/1 N Hydrochloric Acid Interface." Asian Journal of Chemistry 30, no. 8 (2018): 1850–56. http://dx.doi.org/10.14233/ajchem.2018.21344.

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10

Makki, Mohammed Saleh I. T., Reda M. Abdel-Rahman, Hassan M. Faidallah, and Khalid A. Khan. "Synthesis of New Fluorine Substituted Heterocyclic Nitrogen Systems Derived fromp-Aminosalicylic Acid as Antimycobacterial Agents." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/819462.

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Some new fluorine substituted heterocyclic nitrogen systems2–17have been synthesized from ring closure reactions of substitutedp-amino salicylic acids (PAS). The Schiffs base of PAS was cyclized with chloroacetyl chloride and mercaptoacetic acid to give azetidinone2, thiazolidinone3, and spiro-fluoroindolothiazoline-dione10. However, PAS when reacted directly with 4-fluorobenzoyl chloride and 5-oxazolinone yielded derivatives4,5, and7. Aminomethylation of PAS using formaldehyde and piperidine or piperazine formed N-alkyl and N,N′-dialkyl derivatives (11and12respectively) upon fluorinated benzo

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11

Padmanilayam, Maniyan, Bernard Scorneaux, Yuxiang Dong, et al. "Antimalarial activity of N-alkyl amine, carboxamide, sulfonamide, and urea derivatives of a dispiro-1,2,4-trioxolane piperidine." Bioorganic & Medicinal Chemistry Letters 16, no. 21 (2006): 5542–45. http://dx.doi.org/10.1016/j.bmcl.2006.08.046.

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12

Holzgrabe, Ulrike, Willy Friedrichsen, and Karl-F. Hesse. "Keto-Enol-Tautomerism and Configurational Isomerism of 2,6-Disubstituted 4-Piperidone-3,5-dicarboxylates." Zeitschrift für Naturforschung B 46, no. 9 (1991): 1237–50. http://dx.doi.org/10.1515/znb-1991-0918.

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The dialkyl 2,6-dialkylsubstituted 4-piperidone-3,5-dicarboxylates were synthesized by a Mannich procedure. Depending on the substitution at the nitrogen keto-enol-tautomerism and a configurational isomerism at C 2 is observed. The structure of the N-substituted piperidone 24 E (C18H29NO5) has been determined by X-ray analysis: it is characterized by an enol structure of the β-ketoester and an axial position of the alkyl group at C 2 and an equatorial one of the alkyl group at C 6. The O–H···O hydrogen bond shows characteristic values of a strong hydrogen bond. The N-unsubstituted piperidones

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13

Ivanovic, Milovan, I. V. Micovic, Sonja Vuckovic, et al. "The synthesis and pharmacological evaluation of (±)-2, 3- seco-fentanyl analogues." Journal of the Serbian Chemical Society 69, no. 11 (2004): 955–68. http://dx.doi.org/10.2298/jsc0411955i.

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An efficient, five-step synthetic approach to various acyclic 1,3-diamines has been developed and applied to the preparation of a novel class of open-chained fentanyl analogues. The acyclic derivatives 5.1?5.5 (all new compounds) were synthesized with the aim of estimating the significance of the piperidine ring for the opioid analgesic activity of anilido-piperidines. The starting ?-keto-amide 1.1, prepared by the aminolysis of methyl acetoacetate with methylphenethylamine, (93 % yield), was successively reacted with NaH and BuLi, to form the highly reactive ?,?-dienolate anion 1.1a. Regio an

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14

Fustero, Santos, Maria Dolores Díaz, Juan Server Carrió, and Enrique Aguilar. "C−C versus C−N Annulation Reactions of 2-Alkyl-2-oxazolines and 2-Alkyl-2-thiazolines: A Simple Synthesis of Novel 3-Aminoindene, Phthalimidine, Pyrrolidine, and Piperidine Derivatives." European Journal of Organic Chemistry 2001, no. 6 (2001): 1195–201. http://dx.doi.org/10.1002/1099-0690(200103)2001:6<1195::aid-ejoc1195>3.0.co;2-2.

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15

Watanuki, Susumu, Keisuke Matsuura, Yuichi Tomura, et al. "Synthesis and Pharmacological Evaluation of 1-Alkyl-N-[(1R)-1-(4-fluorophenyl)-2-methylpropyl]piperidine-4-carboxamide Derivatives as Novel Antihypertensive Agents." CHEMICAL & PHARMACEUTICAL BULLETIN 59, no. 11 (2011): 1376–85. http://dx.doi.org/10.1248/cpb.59.1376.

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16

Watanuki, Susumu, Keisuke Matsuura, Yuichi Tomura, et al. "Synthesis and pharmacological evaluation of 1-alkyl-N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide derivatives as novel antihypertensive agents." Bioorganic & Medicinal Chemistry 19, no. 18 (2011): 5628–38. http://dx.doi.org/10.1016/j.bmc.2011.07.030.

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17

Gao, Mingzhang, Min Wang, Gary D. Hutchins та Qi-Huang Zheng. "Synthesis of carbon-11-labeled piperidine ring of N-[ω-(6-methoxynaphthalen-1-yl)alkyl] derivatives as new selective PET σ1 receptor probes". Applied Radiation and Isotopes 68, № 3 (2010): 459–65. http://dx.doi.org/10.1016/j.apradiso.2009.12.035.

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18

Fustero, Santos, Maria Dolores Diaz, Juan Server Carrio, and Enrique Aguilar. "ChemInform Abstract: C-C versus C-N Annulation Reactions of 2-Alkyl-2-oxazolines and 2-Alkyl-2-thiazolines: A Simple Synthesis of Novel 3-Aminoindene, Phthalimidine, Pyrrolidine, and Piperidine Derivatives." ChemInform 33, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.200213053.

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19

Perly, Bruno, Giuseppe C. Pappalardo, and Antonio Grassi. "Molecular Determinants for Drug-Receptor Interactions. 6. Proton 500 MHz NMR Spectra of the Narcotic Antagonists Naloxone and Naltrexone by Two-Dimensional 1H–1H Chemical Shift Correlation Spectroscopy." Zeitschrift für Naturforschung B 41, no. 2 (1986): 231–38. http://dx.doi.org/10.1515/znb-1986-0214.

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The full analysis of the 1H NMR spectra of naloxone and naltrexone (hydrochloride salts, in 2H2O solution) was performed by using an high-frequency (500 MHz) spectrometer and the recent technique of two-dimensional (2D ) homonuclear shift spectroscopy. The 1H-1H connectivities allowed detection of correlated resonances and assignments of multiplets. The shapes of the contour levels of the COSY 45 spectra were also used to check the relative signs of coupling constants. The refinement of spectral parameters of some component spin-systems of the complex spectra was performed by computerized iter

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20

Watanuki, Susumu, Keisuke Matsuura, Yuichi Tomura, et al. "ChemInform Abstract: Synthesis and Pharmacological Evaluation of 1-Alkyl-N- [(1R)-1-(4-fluorophenyl)-2-methylpropyl]piperidine-4-carboxamide Derivatives as Novel Antihypertensive Agents." ChemInform 43, no. 17 (2012): no. http://dx.doi.org/10.1002/chin.201217151.

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21

Osipova, Galina V., and Oleg A. Petrov. "CATALYTIC INFLUENCE OF NITROGEN-CONTAINING BASE ON COMPLEXATION OF OCTA(m-TRIFLUOROMETHYLPHENYL)PORPHYRAZINE AND HEXA(m-TRIFLUOROMETHYLPHENYL)BENZOPORPHYRASINE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 6 (2020): 4–11. http://dx.doi.org/10.6060/ivkkt.20206306.6186.

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The review presents data on the complexation of octa(m-trifluoromethylphenyl)porphy-razine and hexa(m-trifluoromethylphenyl)benzoporphyrazine with zinc acetate in a system nitrogen-containing base - benzene. It was shown that the investigated porphyrazines, having pronounced acidic properties at the incyclic NH bonds, interact with n-butylamine, tret-butylamine, morpholine and piperidine in benzene with the formation of proton-transfer complexes. In these complexes, the intocyclic protons of the NH-groups associated with the oxygen atom of the dimethyl sulfoxide molecule and the intocyclic nit

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22

Ivanovic, Milovan, I. V. Micovic, Sonja Vuckovic, et al. "The synthesis and preliminary pharmacological evaluation of racemic cis and trans 3-alkylfentanyl analogues." Journal of the Serbian Chemical Society 69, no. 7 (2004): 511–26. http://dx.doi.org/10.2298/jsc0407511i.

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A general, five step method for the synthesis of 3-alkylfentanyl analogues (i.e., cis and trans 3-alkyl-4-anilidopiperidines 6.1?6.6) has been developed. The starting N-phenethyl- 4-piperidone 1 was first converted into the cyclohexylimine derivative 2, ?-deprotonated with butyllithium and the resulting imine anion efficiently monoalkylated with primary and secondary alkyl halides. After mild acid hydrolysis, the obtained 3-alkyl-4-piperidones 3.1?3.6 were isolated in good yields (79?85 %), then condensed with aniline to form imines 4.1?4.6. Subsequent reduction of the imines (LiAlH4/THF) yiel

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23

Laughton, Charles A., Robert McKenna, Stephen Neidle, Michael Jarman, Ray McCague, and Martin G. Rowlands. "Crystallographic and molecular modeling studies on 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione and its butyl analog, inhibitors of mammalian aromatase. Comparison with natural substrates: prediction of enantioselectivity for N-alkyl derivatives." Journal of Medicinal Chemistry 33, no. 9 (1990): 2673–79. http://dx.doi.org/10.1021/jm00171a052.

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24

Basirat, Narjes, Seyed Sajad Sajadikhah, and Abdolkarim Zare. "Multi-component synthesis of piperidines and dihydropyrrol-2-one derivatives catalyzed by a dual-functional ionic liquid." Journal of Chemical Research 44, no. 1-2 (2019): 20–24. http://dx.doi.org/10.1177/1747519819883881.

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N,N,N’, N’-tetramethyl- N,N’-bis(sulfo)ethane-1,2-diaminium mesylate ([TMBSED][OMs]2) was employed for the synthesis of piperidines and dihydropyrrol-2-ones via one-pot multi-component reactions in simple and green processes. This pseudo five-component reaction of aromatic aldehydes, anilines and alkyl acetoacetates was carried out under reflux conditions in ethanol to afford substituted piperidines. Also, dihydropyrrol-2-one derivatives were synthesized by means of four-component reactions of various amines, dialkyl acetylenedicarboxylates and formaldehyde in ethanol at room temperature. The

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25

Abo-salem, Heba M., Anhar Abdel-aziem, Inas E. Islam, Mariam M. Yossef, and Eslam R. El-sawy. "SYNTHESIS, ANTIMICROBIAL ACTIVITY AND MOLECULAR DOCKING STUDY OF SOME NEW N-BENZYL AND N-BENZOYL-3-INDOLYL HETEROCYCLES." International Journal of Pharmacy and Pharmaceutical Sciences 8, no. 9 (2016): 224. http://dx.doi.org/10.22159/ijpps.2016v8i9.13184.

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<p><strong>Objective: </strong>Chalcones are one of the major classes of the natural products, which display a wide range of pharmacological properties. Also, chalcones are well-known intermediates for synthesizing various heterocyclic compounds like pyrazoline and pyrimidine derivatives. The present work is designed to synthesize new 3-indolylheterocycles starting from <em>N</em>-benzyl and <em>N</em>-benzoyl-1<em>H</em>-indole-3-carboxaldehyds and evaluating theirs <em>in vitro</em> antimicrobial activity. In addition, the pro

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26

Liepa, Andris J., Oanh Nguyen, and Simon Saubern. "Synthesis of Some 4-Oxothiochromenes and Related Compounds." Australian Journal of Chemistry 58, no. 12 (2005): 864. http://dx.doi.org/10.1071/ch05205.

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Thiosalicylic acids react with 2-substituted N,N-dialkyl acetamides to give 3-substituted-N,N-dialkyl-2-amino-4-oxothiochromenes 13. N-Alkyl 2-piperidone and analogous caprolactams give derivatives of 1,2,3,4-tetrahydrothiochromeno[2,3-b]pyridin-5-one 16a–16d and 7,8,9,10-tetrahydro-6H-5-thia-6-aza-cyclohepta-[b]naphthalen-11-one 16e, 16f. 2-Mercaptonicotinic acid gave a 1,2,3,4-tetrahydro-9-thia-1,8-diazaanthracen-10-one 16g and a 1,2,3,4-tetrahydro-9-thia-1,8-diazaanthracene-10-thione 16h.

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27

Sheikh-Ali, Bashir M., Miroslav Rapta, Geoffrey B. Jameson, Changxing Cui, and Richard G. Weiss. "Influence of Alkyl Chain Length on the Fluorescence of Crystalline 4-Alkyl-N-(4-cyanophenyl)piperidines." Journal of Physical Chemistry 98, no. 41 (1994): 10412–18. http://dx.doi.org/10.1021/j100092a005.

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28

Sosnovsky, George, Mikolaj Jawdosiuk, and J. Michael Clumpner. "Di-tert-alkyl Nitroxyl Radicals. Synthesis, Physical Properties and Applications as Inhibitors of Vinyl Polmerization at Elevated Temperatures." Zeitschrift für Naturforschung B 55, no. 1 (2000): 109–26. http://dx.doi.org/10.1515/znb-2000-0118.

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Stable di-tert-alkylnitroxyl radicals, tert-butyl-tert-pentylnitroxyl (4a), di-tert-pentylnitroxyl (4b) and tert-octyl-tert-pentylnitroxyl (4c), the homologs of di-tert-butylnitroxyl (1), were synthesized from tert-alkyl amines 7a-c via the 3-tert-alkylamino-3-methyl-1-butynes 8a-c. Oxidation of 8a,b with hydrogen peroxide lead to relatively unstable N-tert -alkyl-N -(1,1-dimethylprop-2-ynyl)nitroxyl radicals 15a,b. The thermal stability, vapor pressure data, ultraviolet, visible and electron paramagnetic resonance spectra of 4a-c were recorded. The radicals were explored as potential inhibito

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29

Giubellina, Nicola, Wim Aelterman, and Norbert De Kimpe. "Use of 3-halo-1-azaallylic anions in heterocyclic chemistry." Pure and Applied Chemistry 75, no. 10 (2003): 1433–42. http://dx.doi.org/10.1351/pac200375101433.

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The synthetic potential of lithio 3-halo-1-azaallylic anions as building blocks in organic chemistry and especially in heterocyclic chemistry will be highlighted by the synthesis of functionalized imines, obtained after reaction of 3-halo-1-azaallylic anions with het- eroatom-substituted electrophiles. Thus, the latter generated functionalized imines are suitable building blocks for the synthesis of a whole range of heterocycles and physiologically active compounds, including agrochemicals and pharmaceuticals. 3-Halo-1-azaallylic anions were used in the synthesis of N-alkyl-3,3-dichloroazetidi

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30

Sun, Hongbin, Kim M. Millar, Jingsong Yang, Khalil Abboud, and Benjamin A. Horenstein. "A new asymmetric route to substituted piperidines: synthesis of N-alkyl-3,4-dihydroxy-5-alkylpiperidines." Tetrahedron Letters 41, no. 16 (2000): 2801–4. http://dx.doi.org/10.1016/s0040-4039(00)00267-7.

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31

Nguyen, Tom, Dan Sherman, David Ball, Michael Solow, and Bakthan Singaram. "Enantiospecific synthesis of N-benzyl-2-alkyl pyrrolidines and piperidines mediated by chiral organoborane reagents." Tetrahedron: Asymmetry 4, no. 2 (1993): 189–92. http://dx.doi.org/10.1016/s0957-4166(00)82334-4.

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32

Kuznetsov, V. V., L. A. Gaivoronskaya, A. A. Fomichev, R. M. Romero, and N. S. Prostakov. "1-Methyl(benzyl)-2,5-dimethyl-4-N-[aryl(alkyl)amino]piperidines and their acyl derivatives." Chemistry of Heterocyclic Compounds 23, no. 7 (1987): 779–82. http://dx.doi.org/10.1007/bf00475650.

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33

Liang, Gui-Bai, Xiaoxia Qian, Tesfaye Biftu, et al. "Hydroxylated N-alkyl-4-piperidinyl-2,3-diarylpyrrole derivatives as potent broad-spectrum anticoccidial agents." Bioorganic & Medicinal Chemistry Letters 15, no. 20 (2005): 4570–73. http://dx.doi.org/10.1016/j.bmcl.2005.06.096.

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34

Sheikh-ali, Bashir M., and Richard G. Weiss. "Liquid crystalline behaviour from binary mixtures of non-mesogenic 4-alkyl-N-(4-cyanophenyl) piperidines [1]." Liquid Crystals 17, no. 5 (1994): 605–15. http://dx.doi.org/10.1080/02678299408037332.

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35

Sheikh-Ali, Bashir M., C. L. Khetrapal, and Richard G. Weiss. "Orientational Order of Liquid-Crystalline 4-Alkyl-N-(p-cyanophenyl)piperidines by 2H and 13C NMR Spectroscopies." Journal of Physical Chemistry 98, no. 4 (1994): 1213–16. http://dx.doi.org/10.1021/j100055a028.

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36

Sun, Hongbin, Kim M. Millar, Jingsong Yang, Khalil Abboud, and Benjamin A. Horenstein. "ChemInform Abstract: A New Asymmetric Route to Substituted Piperidines: Synthesis of N-Alkyl-3,4-dihydroxy-5-alkylpiperidines." ChemInform 31, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.200030124.

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37

NGUYEN, T., D. SHERMAN, D. BALL, M. SOLOW, and B. SINGARAM. "ChemInform Abstract: Enantiospecific Synthesis of N-Benzyl-2-alkyl Pyrrolidines and Piperidines Mediated by Chiral Organoborane Reagents." ChemInform 24, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199326047.

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38

Kitbunnadaj, Ruengwit, Takeshi Hashimoto, Enzo Poli, et al. "N-Substituted Piperidinyl Alkyl Imidazoles: Discovery of Methimepip as a Potent and Selective Histamine H3Receptor Agonist." Journal of Medicinal Chemistry 48, no. 6 (2005): 2100–2107. http://dx.doi.org/10.1021/jm049475h.

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39

Holzgrabe, U., B. Piening, K. F. Hesse, H. D. Höltje, and M. Worch. "Stereochemistry of 2,6-Dipyridine Substituted N-Benzyl-4-piperidone Mono- and Dicarboxylates and of the Corresponding Reduction Products." Zeitschrift für Naturforschung B 44, no. 5 (1989): 565–74. http://dx.doi.org/10.1515/znb-1989-0512.

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The alkyl N-benzyl-4-piperidone-3-carboxylate (1) is synthesized by a Mannich procedure from pyridine aldehyde, benzylamine and the monoester of acetonedicarboxylate; the corresponding diester 2 is formed by condensation of pyridine aldehyde, benzylamine and dimethyl 3-oxoglutarate. Isomerism is observed with respect to keto-enol tautomerism and cis or trans substitution of the pyridines. The structure of the enol lb (C24H23N3O3) is determined by X-ray analysis: it crystallizes in the triclinic space group P 1̄ with a = 9.965(2), b = 10.476(2), c = 10.838(2) Å, α = 69.48(1), β/3 = 81.56(1), γ

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40

Sheikh-Ali, B. M., M. Rapta, G. B. Jameson, and R. G. Weiss. "Molecular conformations and crystal packing properties of five 4-alkyl-N-(4-cyanophenyl)piperidines by X-ray diffraction: a surprising dependence upon alkyl chain length." Acta Crystallographica Section B Structural Science 51, no. 5 (1995): 823–35. http://dx.doi.org/10.1107/s0108768194013054.

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Flick, Andrew C., and Albert Padwa. "A new route to heterocyclic compounds by the mercuric acetate oxidation of N-alkyl substituted 4-piperidones." Tetrahedron Letters 49, no. 40 (2008): 5739–41. http://dx.doi.org/10.1016/j.tetlet.2008.07.109.

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Liang, Gui-Bai, Xiaoxia Qian, Dennis Feng, et al. "N-Alkyl-4-piperidinyl-2,3-diarylpyrrole derivatives with heterocyclic substitutions as potent and broad spectrum anticoccidial agents." Bioorganic & Medicinal Chemistry Letters 18, no. 6 (2008): 2019–22. http://dx.doi.org/10.1016/j.bmcl.2008.01.104.

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Chinnaraja, Duraisamy, and Ramarajan Rajalakshmi. "Atom and step economic multicomponent synthesis of highly functionalized novel N-alkyl piperidines: structural elucidation through spectral studies and single crystallographic analysis." RSC Adv. 4, no. 78 (2014): 41314–22. http://dx.doi.org/10.1039/c4ra06505k.

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Zhang, Zhao-Fei, Zhong-Hua Gao, Chun-Lin Zhang та Song Ye. "N-heterocyclic carbene-catalyzed intramolecular aza-Michael addition of alkyl amines to α,β-unsaturated carboxylic acid: Synthesis of pyrrolidines and piperidines". Tetrahedron 94 (серпень 2021): 132337. http://dx.doi.org/10.1016/j.tet.2021.132337.

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45

Chinnaraja, Duraisamy, and Ramarajan Rajalakshmi. "ChemInform Abstract: Atom and Step Economic Multicomponent Synthesis of Highly Functionalized Novel N-Alkyl Piperidines: Structural Elucidation Through Spectral Studies and Single Crystallographic Analysis." ChemInform 46, no. 12 (2015): no. http://dx.doi.org/10.1002/chin.201512211.

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Harusawa, Shinya, Koichi Sawada, Takuji Magata, et al. "Synthesis and evaluation of N-alkyl-S-[3-(piperidin-1-yl)propyl]isothioureas: High affinity and human/rat species-selective histamine H3 receptor antagonists." Bioorganic & Medicinal Chemistry Letters 23, no. 23 (2013): 6415–20. http://dx.doi.org/10.1016/j.bmcl.2013.09.052.

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Sheikh-Ali, Bashir M., and Richard G. Weiss. "Effects of Aggregation and Mesomorphic Order on the Photophysical Properties of 4-Alkyl-N-(p-cyanophenyl)piperidines. Molecules Capable of Forming Intramolecular Charge Transfer States." Journal of the American Chemical Society 116, no. 14 (1994): 6111–20. http://dx.doi.org/10.1021/ja00093a008.

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Finke, Paul E., Bryan Oates, Sander G. Mills, et al. "Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 4: synthesis and structure–Activity relationships for 1-[N-(Methyl)-N-(phenylsulfonyl)amino]-2-(phenyl)-4-(4-(N-(alkyl)-N-(benzyloxycarbonyl)amino)piperidin-1-yl)butanes." Bioorganic & Medicinal Chemistry Letters 11, no. 18 (2001): 2475–79. http://dx.doi.org/10.1016/s0960-894x(01)00492-9.

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Finke, Paul E., and et al et al. "ChemInform Abstract: Antagonists of the Human CCR5 Receptor as Anti-HIV-1 Agents. Part 4. Synthesis and Structure-Activity Relationships for 1-[N-(Methyl)-N-(phenylsulfonyl)amino] -2-(phenyl)-4-(4-(N-(alkyl)-N- (benzyloxycarbonyl)amino)piperidin-1-yl)buta." ChemInform 32, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.200149262.

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SHEIKH-ALI, B. M., C. L. KHETRAPAL, and R. G. WEISS. "ChemInform Abstract: Liquid-Crystalline Solvents as Mechanistic Probes. Part 51. Orientational Order of Liquid-Crystalline 4-Alkyl-N-(p-cyanophenyl) piperidines by 2H and 13C NMR Spectroscopy." ChemInform 25, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199423034.

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