Literature DB >> 21286231

Pd-catalyzed amination as an alternative to nucleophilic aromatic substitution for the synthesis of N-alkyltacrines and analogues.

Ming Ma1, Jimit Mehta, Larry D Williams, Paul R Carlier.   

Abstract

A reliable Pd-catalyzed amination protocol is described for the synthesis of N-alkyltacrines and analogues. The Josiphos ligand CyPFtBu was found to provide optimum yields: 16 examples are given. Compared to the typical high-temperature nucleophilic aromatic substitution (NAS) routes, Pd-catalyzed aminations proceed at significantly lower reaction temperatures, and enable the synthesis of otherwise inaccessible products.

Entities:  

Year:  2011        PMID： 21286231      PMCID： PMC3030130          DOI： 10.1016/j.tetlet.2010.12.073

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


  28 in total

1.  Novel and potent tacrine-related hetero- and homobivalent ligands for acetylcholinesterase and butyrylcholinesterase.

Authors:  L Savini; G Campiani; A Gaeta; C Pellerano; C Fattorusso; L Chiasserini; J M Fedorko; A Saxena
Journal:  Bioorg Med Chem Lett       Date:  2001-07-09       Impact factor: 2.823

2.  Dual-site binding of bivalent 4-aminopyridine- and 4-aminoquinoline-based AChE inhibitors: contribution of the hydrophobic alkylene tether to monomer and dimer affinities.

Authors:  Y F Han; C P Li; E Chow; H Wang; Y P Pang; P R Carlier
Journal:  Bioorg Med Chem       Date:  1999-11       Impact factor: 3.641

3.  Synthesis and biological evaluation of NO-donor-tacrine hybrids as hepatoprotective anti-Alzheimer drug candidates.

Authors:  Lei Fang; Dorothea Appenroth; Michael Decker; Michael Kiehntopf; Carolin Roegler; Thomas Deufel; Christian Fleck; Sixun Peng; Yihua Zhang; Jochen Lehmann
Journal:  J Med Chem       Date:  2008-01-31       Impact factor: 7.446

4.  Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.

Authors:  Stefania Butini; Giuseppe Campiani; Marianna Borriello; Sandra Gemma; Alessandro Panico; Marco Persico; Bruno Catalanotti; Sindu Ros; Margherita Brindisi; Marianna Agnusdei; Isabella Fiorini; Vito Nacci; Ettore Novellino; Tatyana Belinskaya; Ashima Saxena; Caterina Fattorusso
Journal:  J Med Chem       Date:  2008-05-15       Impact factor: 7.446

5.  Pyrano[3,2-c]quinoline-6-chlorotacrine hybrids as a novel family of acetylcholinesterase- and beta-amyloid-directed anti-Alzheimer compounds.

Authors:  Pelayo Camps; Xavier Formosa; Carles Galdeano; Diego Muñoz-Torrero; Lorena Ramírez; Elena Gómez; Nicolás Isambert; Rodolfo Lavilla; Albert Badia; M Victòria Clos; Manuela Bartolini; Francesca Mancini; Vincenza Andrisano; Mariana P Arce; M Isabel Rodríguez-Franco; Oscar Huertas; Thomai Dafni; F Javier Luque
Journal:  J Med Chem       Date:  2009-09-10       Impact factor: 7.446

6.  Assembly of 4-aminoquinolines via palladium catalysis: a mild and convenient alternative to SNAr methodology.

Authors:  Brandon J Margolis; Kimberly A Long; Dana L T Laird; J Craig Ruble; Shon R Pulley
Journal:  J Org Chem       Date:  2007-02-13       Impact factor: 4.354

7.  Heterodimeric tacrine-based acetylcholinesterase inhibitors: investigating ligand-peripheral site interactions.

Authors:  P R Carlier; E S Chow; Y Han; J Liu; J El Yazal; Y P Pang
Journal:  J Med Chem       Date:  1999-10-07       Impact factor: 7.446

8.  Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes.

Authors:  Shashank Shekhar; Per Ryberg; John F Hartwig; Jinu S Mathew; Donna G Blackmond; Eric R Strieter; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2006-03-22       Impact factor: 15.419

9.  Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

Authors:  Michael G Organ; Mirvat Abdel-Hadi; Stephanie Avola; Igor Dubovyk; Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Mahmoud Sayah; Cory Valente
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Tacrine-melatonin hybrids as multifunctional agents for Alzheimer's disease, with cholinergic, antioxidant, and neuroprotective properties.

Authors:  María Isabel Fernández-Bachiller; Concepción Pérez; Nuria Eugenia Campillo; Juan Antonio Páez; Gema Cristina González-Muñoz; Paola Usán; Esther García-Palomero; Manuela G López; Mercedes Villarroya; Antonio G García; Ana Martínez; María Isabel Rodríguez-Franco
Journal:  ChemMedChem       Date:  2009-05       Impact factor: 3.466
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