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Mol Divers. 2017 Nov;21(4):893-902. doi: 10.1007/s11030-017-9764-5. Epub 2017 Jul 12.

Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles.

Author information

1
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil. stanley@usp.br.
2
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.
3
Departamento de Física, Universidade Federal de São Carlos, São Carlos, SP, Brazil.
4
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil. hstefani@usp.br.

Abstract

The Ugi multicomponent reaction has been used as an important synthetic route to obtain compounds with potential biological activity. We present the rapid and efficient synthesis of [Formula: see text]-amino-1,3-dicarbonyl compounds in moderate to good yields via Ugi flow chemistry reactions performed with a continuous flow reactor. Such [Formula: see text]-amino-1,3-dicarbonyl compounds can act as precursors for the production of [Formula: see text]-amino acids via hydrolysis of the ethyl ester group as well as building blocks for the synthesis of novel compounds with the 1,2,3-triazole ring. The [Formula: see text]-amino acid derivatives of the Ugi flow chemistry reaction products were then used for dipeptide synthesis.

KEYWORDS:

Click chemistry; Flow chemistry; MRC; Multicomponent reaction; Triazole; Ugi reaction

PMID:
28702849
DOI:
10.1007/s11030-017-9764-5
[Indexed for MEDLINE]

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