Santiago João Victor, Burtoloso Antonio C B
Instituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970 São Carlos, São Paulo, Brazil.
ACS Omega. 2019 Jan 3;4(1):159-168. doi: 10.1021/acsomega.8b02764. eCollection 2019 Jan 31.
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 γ--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 α-diazo imine intermediate, followed by a 5--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%).
三唑是一类重要的氮杂环化合物，以其广泛的生物活性而闻名。在这项工作中，我们希望展示一种罕见的稠合双环[1,2,3] - 三唑的直接合成方法，采用γ-保护的氨基重氮酮作为有用的合成平台。该策略基于三氟乙酰胺基团的脱保护，用于分子内原位生成α-重氮亚胺中间体，然后进行5-exo-dig环化以构建双环单元。通过这种方式，可以以良好至优异的产率（63-95%）进行一系列稠合双环[1,2,3] - 三唑的合成。
