Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

doi:10.3390/molecules14125124

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Molecules 2009, 14(12), 5124-5143; doi:10.3390/molecules14125124

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Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

Michael Klein, Karin Krainz, Itedale Namro Redwan, Peter Dinér and Morten Grøtli*

Department of Chemistry, Medicinal Chemistry, University of Gothenburg, SE-412 96 Göteborg, Sweden

* Author to whom correspondence should be addressed.

Received: 13 November 2009; in revised form: 26 November 2009 / Accepted: 7 December 2009 / Published: 9 December 2009

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Abstract: A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues.

Keywords: [3+2] cycloaddition; azido alcohols; 1,4-disubstituted-1,2,3-triazoles

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MDPI and ACS Style

Klein, M.; Krainz, K.; Redwan, I.N.; Dinér, P.; Grøtli, M. Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids. Molecules 2009, 14, 5124-5143.

AMA Style

Klein M, Krainz K, Redwan IN, Dinér P, Grøtli M. Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids. Molecules. 2009; 14(12):5124-5143.

Chicago/Turabian Style

Klein, Michael; Krainz, Karin; Redwan, Itedale Namro; Dinér, Peter; Grøtli, Morten. 2009. "Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids." Molecules 14, no. 12: 5124-5143.

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