109105-86-4Relevant articles and documents
SSAO INHIBITORS AND USES THEREOF
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Paragraph 00455, (2020/01/08)
Described herein are compounds that are semicarbazide-sensitive amine oxidase (SSAO) inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in treating or preventing a liver disease or condition.
Transition-Metal-Free Deconstructive Lactamization of Piperidines
Romero-Iba?ez, Julio,Cruz-Gregorio, Silvano,Sandoval-Lira, Jacinto,Hernández-Pérez, Julio M.,Quintero, Leticia,Sartillo-Piscil, Fernando
supporting information, p. 8867 - 8871 (2019/05/28)
One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp3)–C(sp3) bonds, which requires using transition or precious metal catalysts. We present here an alternative: the deconstructive lactamization of piperidines without using transition metal catalysts. To this end, we use 3-alkoxyamino-2-piperidones, which were prepared from piperidines through a dual C(sp3)–H oxidation, as transitory intermediates. Experimental and theoretical studies confirm that this unprecedented lactamization occurs in a tandem manner involving an oxidative deamination of 3-alkoxyamino-2-piperidones to 3-keto-2-piperidones, followed by a regioselective Baeyer–Villiger oxidation to give N-carboxyanhydride intermediates, which finally undergo a spontaneous and concerted decarboxylative intramolecular translactamization.
Development of a Robust Process for the Preparation of High-Quality 4-Methylenepiperidine Hydrochloride
Zhu, Fuqiang,Aisa, Haji A.,Zhang, Jian,Hu, Tianwen,Sun, Changliang,He, Yang,Xie, Yuanchao,Shen, Jingshan
, p. 91 - 96 (2018/02/06)
An efficient route for the preparation of 4-methylenepiperidine hydrochloride 1 was designed, and then a process feasible for large-scale production was developed with a total yield of 83.5% at a purity of 99.9%.
Synthesis of Substituted Piperidines from N,N-Bis [(benzotriazol-1 -yl)methyl]amines
Katritzky, Alan R.,Luo, Zhushou,Cui, Xi-Lin
, p. 3328 - 3331 (2007/10/03)
N,N-Bis[(benzotriazol-1-yl)methyl]benzylamines and N,N-bis[(benzotriazol-1-yl)methyl](p-N′,N′-dimethylphenyl)amine on reaction with allyltrimethylsilanes yielded substituted piperidines. Other N,N-bis[(benzotriazol-1-yl)methyl]anilines (unsubstituted and p-CH3, OCH3, Cl) gave julolidines (2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij] quinoline).
An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines
Wu, Xiao-Dong,Khim, Seock-Kyu,Zhang, Xiaoming,Cederstrom, Ericka M.,Mariano, Patrick S.
, p. 841 - 859 (2007/10/03)
Studies focusing on the development and application of a new oxidative methodology for promoting Mannich cyclizations have been conducted. The general features of these processes were explored with selected α-silylamino and α-silylamido allyl- and vinylsilanes. Representative conditions for affecting conversion of the α-silylamine and -amide functionalities into intermediate N-alkyl and N-acyliminium cations involve either 9,10-dicyanoanthracene SET-sensitized photooxidation or ceric ammonium or tetra-n-butylammonium nitrate oxidations. The applicability of these procedures for promoting Mannich cyclizations was first demonstrated by the preparation of methylidenepi- peridines and -hydroazepines. Further studies have led to observations which show that Mannich cyclizations of stereochemically labeled α-silylamino vinylsilanes proceed to furnish tetrahydro- pyridines. Also, unlike their amine analogues, α-silylamido (E)-vinylsilanes undergo cyclization to produce tetrahydropyridines with retention of absolute and relative stereochemistry. The differences are due to the fact that N-acyliminium cations serve as intermediates in reactions of the α-silylamide systems. Moreover, the oxidation procedure is ideally suited for intermediate N-acyliminium cation generation in stereocontrolled reactions of α-silylamido allylsilanes. Finally, the preparative utility of the new cyclization method, when used in conjunction with an α-amino acid based strategy for substrate generation, was demonstrated by applications in concise routes for the synthesis of the aza-sugars, (-)-1-deoxymannojirimycin and (+)-l-deoxyallonojirimycin.
Synthesis and evaluation of (piperidinomethylene)bis(phosphonic acid) derivatives as anti-osteoporosis agents
Mimura,Hayashida,Nomiyama,Ikegami,Iida,Tamura,Hiyama,Ohishi
, p. 1971 - 1986 (2007/10/02)
Some (piperidinomethylene)bis(phosphonic acid) derivatives were prepared and their activity to inhibit a rise in serum calcium induced by parathyroid hormone in thyroparathyroidectomised rats was evaluated. Several (4- alkylidene-, 4,4-dialkyl-, or 4-alkyl-4- halopiperidinomethylene)bis(phosphonic acid) derivatives showed considerable inhibitory activity. But compounds having aromatic and polar substituents such as azido, hydroxy, amino and amido on the piperidine ring were generally inactive. In this study, two 4-alkylidene compounds (8a and 8b) and a 4,4- cyclic dialkyl compound (61) showed potent activity when administered either intravenously or perorally.
Oxidative methods for promoting iminium cation cyclization reactions
Zhang,Jung,Mariano,Fox,Martin,Merkert
, p. 5239 - 5242 (2007/10/02)
A new methodology for promoting iminium cation cyclization reactions, involving oxidation of α-silylamines, is presented.
INTRAMOLECULAR VARIANTS OF AMINOMETHANO DESILYLATION: REACTIONS OF IN SITU GENERATED IMMONIUM IONS WITH ALLYLSILANES
Grieco, Paul A.,Fobare, William F.
, p. 5067 - 5070 (2007/10/02)
Intramolecular condensation of immonium ions with allylsilanes in aqueous tetrahydrofuran at ambient temperature gives rise to five, six, seven, and eight-membered rings containing nitrogen.
