Synthesis of Fused Bicyclic [1,2,3]-Triazoles from gamma-Amino Diazoketones

Author(s)

Santiago, Joao Victor ^[1] ; Burtoloso, Antonio C. B. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: ACS OMEGA; v. 4, n. 1, p. 159-168, JAN 2019.
• Web of Science Citations: 0

Abstract

Triazoles are an important class of N-heterocycles that are well known for their broad biological activities. In this work, we would like to demonstrate a direct synthesis of the rare fused bicyclic {[}1,2,3]-triazoles, employing gamma-N-protected amino diazoketones as useful synthetic platforms. The strategy was based on the deprotection of a trifluoroacetamide group for the intramolecular and in situ generation of an a-diazo imine intermediate, followed by a 5-endo-dig cyclization to construct the bicyclic unit. In this fashion, the synthesis of a series of fused bicyclic {[}1,2,3]-triazoles could be carried out in good to excellent yields (63-95%). (AU)

• FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
• Grantee: Carlos Alberto Montanari
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 13/25504-1 - Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/23329-9 - Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants