Literature DB >> 31762498

Pd-catalyzed arylation of linear and angular spirodiamine salts under aerobic conditions.

Sean W Reilly1, Nikaela W Bryan2, Robert H Mach1.   

Abstract

Application of Buchwald-Hartwig catalysis for development of biologically relevant arylspirodiamine compounds is reported. This synthetic methodology requires no inert atmosphere and affords yields up to 93% in just 20 min. Linear and sterically hindered angular spirodiamines in salt and free-base form are coupled with electron-rich and -withdrawing aryl chlorides, demonstrating a broad scope and applicability of this protocol.

Entities:  

Keywords:  Arylation; C-N cross-coupling; Pd cross-coupling; RuPhos; Spirodiamine

Year:  2016        PMID： 31762498      PMCID： PMC6874415          DOI： 10.1016/j.tetlet.2016.12.063

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


  35 in total

Review 1.  New and unusual scaffolds in medicinal chemistry.

Authors:  Charles M Marson
Journal:  Chem Soc Rev       Date:  2011-08-12       Impact factor: 54.564

2.  Spirocyclic nonpeptide glycoprotein IIb-IIIa antagonists. Part 3: synthesis and SAR of potent and specific 2,8-diazaspiro[4.5]decanes.

Authors:  Mukund M Mehrotra; Julie A Heath; Jack W Rose; Mark S Smyth; Joseph Seroogy; Deborah L Volkots; Gerd Ruhter; Theo Schotten; Lisa Alaimo; Gary Park; Anjali Pandey; Robert M Scarborough
Journal:  Bioorg Med Chem Lett       Date:  2002-04-08       Impact factor: 2.823

3.  Pd-Catalyzed Synthesis of Piperazine Scaffolds Under Aerobic and Solvent-Free Conditions.

Authors:  Sean W Reilly; Robert H Mach
Journal:  Org Lett       Date:  2016-10-13       Impact factor: 6.005

4.  Synthesis and pharmacological evaluation of piperidine (piperazine)-substituted benzoxazole derivatives as multi-target antipsychotics.

Authors:  Ling Huang; Wenjun Zhang; Xiaohua Zhang; Lei Yin; Bangyin Chen; Jinchun Song
Journal:  Bioorg Med Chem Lett       Date:  2015-09-21       Impact factor: 2.823

5.  Expanding the azaspiro[3.3]heptane family: synthesis of novel highly functionalized building blocks.

Authors:  Johannes A Burkhard; Carine Guérot; Henner Knust; Erick M Carreira
Journal:  Org Lett       Date:  2011-11-23       Impact factor: 6.005

6.  Spirocyclic nonpeptide glycoprotein IIb-IIIa antagonists. Part 2: design of potent antagonists containing the 3-azaspiro[5.5]undecanes.

Authors:  A Pandey; J Seroogy; D Volkots; M S Smyth; J Rose; M M Mehrotra; J Heath; G Ruhter; T Schotten; R M Scarborough
Journal:  Bioorg Med Chem Lett       Date:  2001-05-21       Impact factor: 2.823

7.  Synthesis and anticancer activity evaluation of some benzothiazole-piperazine derivatives.

Authors:  Enise Ece Gurdal; Ebru Buclulgan; Irem Durmaz; Rengul Cetin-Atalay; Mine Yarim
Journal:  Anticancer Agents Med Chem       Date:  2015       Impact factor: 2.505

8.  2,6-Diazaspiro[3.3]heptanes: synthesis and application in Pd-catalyzed aryl amination reactions.

Authors:  Johannes Burkhard; Erick M Carreira
Journal:  Org Lett       Date:  2008-07-17       Impact factor: 6.005

Review 9.  Spiro skeletons: a class of privileged structure for chiral ligand design.

Authors:  Kuiling Ding; Zhaobin Han; Zheng Wang
Journal:  Chem Asian J       Date:  2009-01-05

Review 10.  Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism.

Authors:  John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  1998-08-17       Impact factor: 15.336
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  1 in total

1.  Exploration of Diazaspiro Cores as Piperazine Bioisosteres in the Development of σ2 Receptor Ligands.

Authors:  Kuiying Xu; Chia-Ju Hsieh; Ji Youn Lee; Aladdin Riad; Nicholas J Izzo; Gary Look; Susan Catalano; Robert H Mach
Journal:  Int J Mol Sci       Date:  2022-07-27       Impact factor: 6.208
  1 in total

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