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

• Published in: Molecular diversity Vol. 21; no. 4; pp. 893 - 902
• Main Authors: Vasconcelos, Stanley N. S., Fornari, Evelin, Caracelli, Ignez, Stefani, Hélio A.
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 01.11.2017; Springer Nature B.V
• Subjects: Aldehydes - chemistry; Biochemistry; Biomedical and Life Sciences; Chemical compounds; Chemical reactions; Chemical synthesis; Chemistry; Chemistry Techniques, Synthetic; Click Chemistry; Continuous flow; Life Sciences; Models, Molecular; Molecular Conformation; Organic Chemistry; Original Article; Pharmacy; Polymer Sciences; Stereoisomerism; Triazoles - chemical synthesis; Triazoles - chemistry; Triazole; Multicomponent reaction; Click chemistry; Ugi reaction; Flow chemistry; MRC
• ISSN: 1381-1991; 1573-501X
• DOI: 10.1007/s11030-017-9764-5

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 α -amino-1,3-dicarbonyl compounds in moderate to good yields via Ugi flow chemistry reactions performed with a continuous flow reactor. Such α -amino-1,3-dicarbonyl compounds can act as precursors for the production of α -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 α -amino acid derivatives of the Ugi flow chemistry reaction products were then used for dipeptide synthesis.