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Literature DB >> 21666850

Superelectrophilic chemistry of amino-nitriles and related substrates.

Abstract

The superacid-promoted Houben-Hoesch reactions of amino-nitriles and related compounds have been studied. The nitriles form dicationic electrophiles and react with benzene in fair to good yields (12-95%). The intermediate iminium ions may also be reduced to the benzylic amines by NaBH(4) or H(2).

Entities: Chemical Disease

Year: 2011 PMID： 21666850 PMCID： PMC3110710 DOI： 10.1016/j.tet.2011.04.038

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

3 in total

1. Diastereoselective aldolization of alpha-aminonitriles. Diastereoselective synthesis of beta-amino alcohols and beta,gamma-diamino alcohols.

Authors: Eric Leclerc; Emmanuel Vrancken; Pierre Mangeney
Journal: J Org Chem Date: 2002-12-13 Impact factor: 4.354

2. NMR-guided fragment-based approach for the design of tRNA(Lys3) ligands.

Authors: Florence Chung; Carine Tisné; Thomas Lecourt; Frédéric Dardel; Laurent Micouin
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Scaffold oriented synthesis. Part 2: Design, synthesis and biological evaluation of pyrimido-diazepines as receptor tyrosine kinase inhibitors.

Authors: Vijaya Gracias; Zhiqin Ji; Irini Akritopoulou-Zanze; Cele Abad-Zapatero; Jeffrey R Huth; Danying Song; Philip J Hajduk; Eric F Johnson; Keith B Glaser; Patrick A Marcotte; Lori Pease; Nirupama B Soni; Kent D Stewart; Steven K Davidsen; Michael R Michaelides; Stevan W Djuric
Journal: Bioorg Med Chem Lett Date: 2008-03-10 Impact factor: 2.823

3 in total

Superelectrophilic chemistry of amino-nitriles and related substrates.

1. Diastereoselective aldolization of alpha-aminonitriles. Diastereoselective synthesis of beta-amino alcohols and beta,gamma-diamino alcohols.

2. NMR-guided fragment-based approach for the design of tRNA(Lys3) ligands.

3. Scaffold oriented synthesis. Part 2: Design, synthesis and biological evaluation of pyrimido-diazepines as receptor tyrosine kinase inhibitors.

1. Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions.

2. Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine.

3. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.