Literature DB >> 15151394

Photochemical preparation of 1,3,5,7-tetracyanoadamantane and its conversion to 1,3,5,7-tetrakis(aminomethyl)adamantane.

Ging S Lee1, Jude N Bashara, Ghiwa Sabih, Asmik Oganesyan, Gayane Godjoian, Hieu M Duong, Eric R Marinez, Carlos G Gutiérrez.   

Abstract

New adamantane derivatives 1 and 2 that bear functionalized one-carbon extensions at all four bridgehead positions have been prepared. Radical nucleophilic substitution (S(RN)1) reaction of 1,3,5,7-tetrabromoadamantane with cyanide produces 1,3,5,7-tetracyanoadamantane (1), which was reduced with borane reagents to 1,3,5,7-tetrakis(aminomethyl)adamantane (2). Improvements in the preparation of 1,3,5,7-tetrahaloadamantanes (halogen = Br, Cl, I) are also reported. [structure--see text]

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Year:  2004        PMID: 15151394     DOI: 10.1021/ol036526g

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Synthesis of rigid multivalent scaffolds based on adamantane.

Authors:  Wolfgang Maison; John V Frangioni; Nadine Pannier
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005

2.  Rigid multivalent scaffolds based on adamantane.

Authors:  Khaled Nasr; Nadine Pannier; John V Frangioni; Wolfgang Maison
Journal:  J Org Chem       Date:  2008-01-08       Impact factor: 4.354

Review 3.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

4.  The Symmetric Tetravalent Sulfhydryl-Specific Linker NATBA Facilitates a Combinatorial "Tool Kit" Strategy for Phage Display-Based Selection of Functionalized Bicyclic Peptides.

Authors:  Christoph Ernst; Julia Sindlinger; Dirk Schwarzer; Pierre Koch; Frank M Boeckler
Journal:  ACS Omega       Date:  2018-10-01
  4 in total

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