Literature DB >> 23316094

A novel synthesis of 1-aryl-3-piperidone derivatives.

Yinan Zhang1, Richard B Silverman.   

Abstract

A novel method to construct the 1-aryl-3-piperidone scaffold is described here. Starting from 3,5-dichloroaniline, a seven-step synthesis, without the use of protecting groups, generates the desired 3-piperidone ring in an overall yield of 30% through a key Morita-Baylis-Hillman reaction and ring-closing metathesis, providing easy access to diverse and useful heterocycles.

Entities:  

Year:  2013        PMID： 23316094      PMCID： PMC3541782          DOI： 10.1016/j.tetlet.2012.11.085

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


  11 in total

Review 1.  Recent contributions from the Baylis-Hillman reaction to organic chemistry.

Authors:  Deevi Basavaiah; Bhavanam Sekhara Reddy; Satpal Singh Badsara
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

Review 2.  Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

Authors:  Georgios C Vougioukalakis; Robert H Grubbs
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

3.  The efficacy of sodium channel blockers to prevent phencyclidine-induced cognitive dysfunction in the rat: potential for novel treatments for schizophrenia.

Authors:  Charles H Large; Silvia Bison; Ilaria Sartori; Kevin D Read; Alessandro Gozzi; Davide Quarta; Marinella Antolini; Emma Hollands; Catherine H Gill; Martin J Gunthorpe; Nagi Idris; Jo C Neill; Giuseppe S Alvaro
Journal:  J Pharmacol Exp Ther       Date:  2011-04-12       Impact factor: 4.030

4.  Synthesis and in vitro antibacterial activity of 7-(3-alkoxyimino-4-amino-4-methylpiperidin-1-yl) fluoroquinolone derivatives.

Authors:  Ju-Xian Wang; Yi-Bin Zhang; Ming-Liang Liu; Bo Wang; Yun Chai; Su-Jie Li; Hui-Yuan Guo
Journal:  Eur J Med Chem       Date:  2011-03-23       Impact factor: 6.514

5.  Direct amination of γ-halo-β-ketoesters with anilines.

Authors:  Yinan Zhang; Richard B Silverman
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

6.  ADME-guided design and synthesis of aryloxanyl pyrazolone derivatives to block mutant superoxide dismutase 1 (SOD1) cytotoxicity and protein aggregation: potential application for the treatment of amyotrophic lateral sclerosis.

Authors:  Tian Chen; Radhia Benmohamed; Jinho Kim; Karen Smith; Daniel Amante; Richard I Morimoto; Donald R Kirsch; Robert J Ferrante; Richard B Silverman
Journal:  J Med Chem       Date:  2011-12-22       Impact factor: 7.446

7.  Enantioselective synthesis of cyclic amides and amines through mo-catalyzed asymmetric ring-closing metathesis.

Authors:  Elizabeth S Sattely; G Alexander Cortez; David C Moebius; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Synthesis of a series of 4-benzyloxyaniline analogues as neuronal N-type calcium channel blockers with improved anticonvulsant and analgesic properties.

Authors:  L Y Hu; T R Ryder; M F Rafferty; M R Feng; S M Lotarski; D M Rock; M Sinz; S J Stoehr; C P Taylor; M L Weber; S S Bowersox; G P Miljanich; E Millerman; Y X Wang; B G Szoke
Journal:  J Med Chem       Date:  1999-10-07       Impact factor: 7.446

Review 9.  The enantioselective Morita-Baylis-Hillman reaction and its aza counterpart.

Authors:  Géraldine Masson; Christopher Housseman; Jieping Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Olefin ring closing metathesis and hydrosilylation reaction in aqueous medium by Grubbs second generation ruthenium catalyst.

Authors:  Vivek Polshettiwar; Rajender S Varma
Journal:  J Org Chem       Date:  2008-08-22       Impact factor: 4.354
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