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Literature DB >> 24511163

Efficient synthesis of cis-2,6-di-(2- quinolylpiperidine).

Derong Ding¹, Linda P Dwoskin¹, Peter A Crooks².

Abstract

An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl- methyl)quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.

Entities: Chemical Disease Gene Species

Keywords: Lobelane; Swern oxidation; Wittig reaction; cis-2,6-di-(2-quinolylpiperidine); norlobelane analogues; quinlobelane

Year: 2013 PMID： 24511163 PMCID： PMC3914661 DOI： 10.1016/j.tetlet.2013.07.067

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

3 in total

1. Quinlobelane: a water-soluble lobelane analogue and inhibitor of VMAT2.

Authors: Ashish P Vartak; A Gabriela Deaciuc; Linda P Dwoskin; Peter A Crooks
Journal: Bioorg Med Chem Lett Date: 2010-05-04 Impact factor: 2.823

2. Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.

Authors: Guangrong Zheng; Linda P Dwoskin; Agripina G Deaciuc; Seth D Norrholm; Peter A Crooks
Journal: J Med Chem Date: 2005-08-25 Impact factor: 7.446

3. Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2.

Authors: Guangrong Zheng; Linda P Dwoskin; Agripina G Deaciuc; Peter A Crooks
Journal: Bioorg Med Chem Lett Date: 2008-10-14 Impact factor: 2.823

3 in total

1. Quinolyl analogues of norlobelane: novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake at the vesicular monoamine transporter-2.

Authors: Derong Ding; Justin R Nickell; Linda P Dwoskin; Peter A Crooks
Journal: Bioorg Med Chem Lett Date: 2015-05-09 Impact factor: 2.823

2. Synthesis of Lobeline, Lobelane and their Analogues. A Review.

Authors: Guangrong Zheng; Peter A Crooks
Journal: Org Prep Proced Int Date: 2015-08-17 Impact factor: 1.628

3. KO ^t Bu-promoted oxidative dimerizations of 2-methylquinolines to 2-alkenyl bisquinolines with molecular oxygen.

Authors: Zhen Wang; Jinjin Zhang; Jianxue Shi; Huiqiao Wang
Journal: RSC Adv Date: 2019-09-23 Impact factor: 4.036

3 in total

Efficient synthesis of cis-2,6-di-(2- quinolylpiperidine).

1. Quinlobelane: a water-soluble lobelane analogue and inhibitor of VMAT2.

2. Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter.

3. Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2.

1. Quinolyl analogues of norlobelane: novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake at the vesicular monoamine transporter-2.

2. Synthesis of Lobeline, Lobelane and their Analogues. A Review.

3. KO t Bu-promoted oxidative dimerizations of 2-methylquinolines to 2-alkenyl bisquinolines with molecular oxygen.

3. KO ^t Bu-promoted oxidative dimerizations of 2-methylquinolines to 2-alkenyl bisquinolines with molecular oxygen.