Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 1508-1516Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.172
Keywords
beta-amino acids; click chemistry; continuous-flow; copper; flow chemistry; triazoles
Categories
Funding
- National Excellence Program [TAMOP 4.2.4. A/2-11-1-2012-0001]
- European Union
- European Social Fund
- Hungarian Academy of Sciences
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The preparation of novel multi-substituted 1,2,3-triazole-modified beta-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 beta-aminocyclohexanecarboxylates can be regarded as interesting precursors for drugs with possible biological effects.
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