Rentería-Gómez Manuel A, Calderón-Rangel David, Corona-Díaz Alejandro, Gámez-Montaño Rocío
Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato, C.P. 36050, Gto., México.
Chempluschem. 2025 Jan;90(1):e202400455. doi: 10.1002/cplu.202400455. Epub 2024 Nov 8.
Bis-heterocycles were synthesized via a consecutive one-pot process by a Groebke-Blackburn-Bienaymé reaction (GBB-3CR) followed by Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) assisted by alternative sustainable energies (ASE) such as ultrasonic and mechanical. These efficient and convergent strategies allowed the in situ generation of complex azides functionalized with imidazo[1,2-a]pyridines (IMPs), which was used as a synthetic platform. The target molecules contain two privileged scaffolds in medicinal chemistry: IMPs and the heterocyclic bioisostere of trans-amide bond, the 1,4-disubstituted 1H-1,2,3-triazoles (1,4-DS-1,2,3-Ts).
双杂环化合物是通过连续一锅法,经由格罗布克-布莱克本-比内梅反应(GBB-3CR),随后在超声和机械等替代可持续能源(ASE)辅助下进行铜催化的炔烃-叠氮环加成反应(CuAAC)合成的。这些高效且汇聚的策略使得能够原位生成用咪唑并[1,2-a]吡啶(IMPs)官能化的复杂叠氮化物,其被用作合成平台。目标分子在药物化学中包含两个优势骨架:IMPs以及反式酰胺键的杂环生物电子等排体,即1,4-二取代的1H-1,2,3-三唑(1,4-DS-1,2,3-Ts)。