52003-32-4Relevant academic research and scientific papers
Total synthesis of (±)-20: S -hydroxy-1,2-dehydro-pseudoaspidospermidine via a C-H activation/transannular cyclization strategy
Leitner, Christian,Gaich, Tanja
supporting information, p. 7451 - 7453 (2017/07/12)
A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.
High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4- epoxypiperidines with amines - A short-step synthesis of 4- fluorobenzyltrozamicol and novel anilidopiperidines
Scheunemann, Matthias,Hennig, Lothar,Funke, Uta,Steinbach, J?rg
, p. 3448 - 3456 (2011/06/20)
Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4- fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new β-hydroxy substituted anilidopiperidines.
Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks
Gijsen, Harrie J.M.,De Cleyn, Michel J.A.,Love, Christopher J.,Surkyn, Michel,Van Brandt, Sven F.A.,Verdonck, Marc G.C.,Moens, Luc,Cuypers, Jef,Bosmans, Jean-Paul R.M.A.
, p. 2456 - 2464 (2008/09/18)
Two diastereoselective, scaleable routes towards trans-3,4-disubstituted piperidines with a 4-hydroxymethyl-3-hydroxy or 4-aminomethyl-3-hydroxy substitution pattern are being described. In the first route, the 3,4-trans configuration was introduced regio- and diastereoselectively via a hydroboration/oxidation sequence starting from 4-hydroxymethylpyridine. In the second route, regioselective epoxide ring opening of N-benzyl-3,4-epoxy-piperidine was achieved with LiCN, in situ generated from acetocyanohydrin and LiNH2. The regioselectivity of both the hydroboration and the epoxide ring opening was positively influenced by the presence of the basic piperidine nitrogen. Both routes have been optimized to be performed at large scale.
Synthesis and antibacterial activity of novel fluoroquinolones containing substituted piperidines
Dang, Zhao,Yang, Yushe,Ji, Ruyun,Zhang, Shuhua
, p. 4523 - 4526 (2008/02/12)
The design and synthesis of new fluoroquinolone antibacterial agents having substituted piperidine rings at the C-7 position are described. Most of the new compounds demonstrated high in vitro antibacterial activity. Several of them exhibited significant activities against Gram-positive organisms, which were more potent than those of gemifloxacin, Linezolid, and vancomycin.
PYRROLOTRIAZINE COMPOUNDS AS KINASE INHIBITORS
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Page/Page column 80-81, (2008/06/13)
The present invention provides compounds of formula (I); and pharmaceutically acceptable salts thereof. The formula (I) compounds inhibit tyrosine kinase activity of growth factor receptors such as HER1, HER2 and HER4 thereby making them useful as antiproliferative agents. The formula (I) compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.
Practical synthesis of ethyl cis-4-amino-3-methoxy-1-piperidine carboxylate, a key intermediate of cisapride
Kim,Pyun,Jung,Kwak,Kim,Kim,Jeong,Lee
, p. 1081 - 1089 (2007/10/03)
A practical synthesis of ethyl cis-4-amino-3-methoxy-1piperidinecarboxylate 1, a key intermediate of cisapride as a potent gastrointestinal stimulant, has been accomplished from 1-methyl-1,2,3,6-tetrahydropyridine 2 via an efficient formation of cis-fused oxazolidinopiperidine 7.
Synthesis and Dynamic NMR Studies of the 3,7-Diazabicycloheptane System
Majchrzak, Michal,Kotelko, Antoni,Lambert, Joseph B.
, p. 539 - 543 (2007/10/02)
A new bicyclic system, 3,7-diazabicycloheptane, has been prepared from 3-(ethoxycarbonyl)-7,3-oxazabicycloheptane by reaction with sodium azide and reduction of the resulting tosyloxy azide with lithium aluminum hydride.The molecule can exis
1,6-Dihydro-3(2H)-pyridinones. I. Facile Synthesis of N-Substituted 1,6-Dihydro-3(2H)-pyridinones
Iamanishi, Takeshi,Shin, Hiroaki,Hanaoka, Miyoji,Momose, Takefumi,Imanishi, Ichiro
, p. 3617 - 3623 (2007/10/02)
The first synthesis of the N-substituted 1,6-dihydro-3(2H)-pyridinones (4 and 16) is described. 1-Benzyl-1,2,3,6-tetrahydropyridine (9) was treated with ethyl chloroformate to give the urethane (6), which was oxidized to the epoxide (10) with perbenzoic a
