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

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 rea...

Full description

Bibliographic Details
Main Authors:	Morten Grøtli, Peter Dinér, Karin Krainz, Itedale Namro Redwan, Michael Klein
Format:	Article
Language:	English
Published:	MDPI AG 2009-12-01
Series:	Molecules
Subjects:	[3+2] cycloaddition azido alcohols 1,4-disubstituted-1,2,3-triazoles
Online Access:	http://www.mdpi.com/1420-3049/14/12/5124/

id	doaj-4368f4b501f943ef9102215eab2b0dfc
record_format	Article
spelling	doaj-4368f4b501f943ef9102215eab2b0dfc2020-11-24T22:35:15ZengMDPI AGMolecules1420-30492009-12-0114125124514310.3390/molecules14125124Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino AcidsMorten GrøtliPeter DinérKarin KrainzItedale Namro RedwanMichael KleinA 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. http://www.mdpi.com/1420-3049/14/12/5124/[3+2] cycloadditionazido alcohols1,4-disubstituted-1,2,3-triazoles
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Morten Grøtli Peter Dinér Karin Krainz Itedale Namro Redwan Michael Klein
spellingShingle	Morten Grøtli Peter Dinér Karin Krainz Itedale Namro Redwan Michael Klein Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids Molecules [3+2] cycloaddition azido alcohols 1,4-disubstituted-1,2,3-triazoles
author_facet	Morten Grøtli Peter Dinér Karin Krainz Itedale Namro Redwan Michael Klein
author_sort	Morten Grøtli
title	Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids
title_short	Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids
title_full	Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids
title_fullStr	Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids
title_full_unstemmed	Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids
title_sort	synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2009-12-01
description	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.
topic	[3+2] cycloaddition azido alcohols 1,4-disubstituted-1,2,3-triazoles
url	http://www.mdpi.com/1420-3049/14/12/5124/
work_keys_str_mv	AT mortengrøtli synthesisofchiral14disubstituted123triazolederivativesfromaminoacids AT peterdiner synthesisofchiral14disubstituted123triazolederivativesfromaminoacids AT karinkrainz synthesisofchiral14disubstituted123triazolederivativesfromaminoacids AT itedalenamroredwan synthesisofchiral14disubstituted123triazolederivativesfromaminoacids AT michaelklein synthesisofchiral14disubstituted123triazolederivativesfromaminoacids
_version_	1725724393387065344

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

Similar Items