Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

The preparation of novel multi-substituted 1,2,3-triazole-modified β-aminocyclohexanecarboxylic acid derivatives in a simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially,...

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Main Authors:	Sándor B. Ötvös, Ádám Georgiádes, István M. Mándity, Lóránd Kiss, Ferenc Fülöp
Format:	Article
Language:	English
Published:	Beilstein-Institut 2013-07-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	β-amino acids click chemistry continuous-flow copper flow chemistry triazoles
Online Access:	https://doi.org/10.3762/bjoc.9.172

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spelling	doaj-31d4763fb84e4bf9aba928ae5ff1b95f2021-02-02T05:36:42ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-07-01911508151610.3762/bjoc.9.1721860-5397-9-172Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale productionSándor B. Ötvös0Ádám Georgiádes1István M. Mándity2Lóránd Kiss3Ferenc Fülöp4Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryThe preparation of novel multi-substituted 1,2,3-triazole-modified β-aminocyclohexanecarboxylic acid derivatives in a simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially, high reaction rates were achieved under high-pressure/high-temperature conditions. Subsequently, the reaction temperature was lowered to room temperature by the joint use of both basic and acidic additives to improve the safety of the synthesis, as azides were to be handled as unstable reactants. Scale-up experiments were also performed, which led to the achievement of gram-scale production in a safe and straightforward way. The obtained 1,2,3-triazole-substituted β-aminocyclohexanecarboxylates can be regarded as interesting precursors for drugs with possible biological effects.https://doi.org/10.3762/bjoc.9.172β-amino acidsclick chemistrycontinuous-flowcopperflow chemistrytriazoles
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Sándor B. Ötvös Ádám Georgiádes István M. Mándity Lóránd Kiss Ferenc Fülöp
spellingShingle	Sándor B. Ötvös Ádám Georgiádes István M. Mándity Lóránd Kiss Ferenc Fülöp Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production Beilstein Journal of Organic Chemistry β-amino acids click chemistry continuous-flow copper flow chemistry triazoles
author_facet	Sándor B. Ötvös Ádám Georgiádes István M. Mándity Lóránd Kiss Ferenc Fülöp
author_sort	Sándor B. Ötvös
title	Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
title_short	Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
title_full	Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
title_fullStr	Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
title_full_unstemmed	Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
title_sort	efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2013-07-01
description	The preparation of novel multi-substituted 1,2,3-triazole-modified β-aminocyclohexanecarboxylic acid derivatives in a simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially, high reaction rates were achieved under high-pressure/high-temperature conditions. Subsequently, the reaction temperature was lowered to room temperature by the joint use of both basic and acidic additives to improve the safety of the synthesis, as azides were to be handled as unstable reactants. Scale-up experiments were also performed, which led to the achievement of gram-scale production in a safe and straightforward way. The obtained 1,2,3-triazole-substituted β-aminocyclohexanecarboxylates can be regarded as interesting precursors for drugs with possible biological effects.
topic	β-amino acids click chemistry continuous-flow copper flow chemistry triazoles
url	https://doi.org/10.3762/bjoc.9.172
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Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

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