Aminoalkylations of Esters, Sulfones, Sulfoxides, Alkylated Pyridines, and Nitriles with in situ Generated Iminium Ions

Alan R. Katritzky; Krzysztof R. Idzik; Ashraf A. A. Abdel-Fattah; Jadwiga Soloducho; Peter J. Steel

doi:10.1055/s-2006-949463

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Synthesis 2006(20): 3377-3388
DOI: 10.1055/s-2006-949463

PAPER

Aminoalkylations of Esters, Sulfones, Sulfoxides, Alkylated Pyridines, and Nitriles with in situ Generated Iminium Ions

Alan R. Katritzky*^a, Krzysztof R. Idzik^a,b, Ashraf A. A. Abdel-Fattah^a,c, Jadwiga Soloducho^b, Peter J. Steel^d
^a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
e-Mail: katritzky@chem.ufl.edu;
^b Department of Chemistry, Faculty of Medical Chemistry and Microbiology, Wroclaw University of Technology, Wybrzeże Wyspianskiego 27, 50-370 Wroclaw, Poland
^c Department of Chemistry, , Benha University, Benha, Egypt
^d Department of Chemistry, University of Canterbury, Chirstchurch, New Zealand

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Publication History

Received 13 April 2006
Publication Date:
10 October 2006 (online)

Abstract
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Abstract

N-(α-Aminoalkyl)benzotriazoles, prepared from a variety of aldehydes and secondary amines, react with diverse ester enolates, sulfones, a sulfoxide, alkylated pyridines, and nitriles to provide novel access to β-amino carboxylic esters (55-80% yield), β-aminoalkyl sulfones (42-88% yield), β-aminoalkyl sulfoxides (20-32% yield), α- and γ-(β-aminoalkyl)pyridines (69-90% yield), and β-aminoalkyl cyanides (10-97% yield), respectively.

Key words

benzotriazoles - β-amino esters - β-aminoalkyl sulfones - pyridines - β-aminoalkyl cyanides

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