Gorachand Badaraita, Surendra Reddy Gundam, Ramachary Dhevalapally B
Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad500 046, India.
ACS Org Inorg Au. 2024 Jun 5;4(5):534-544. doi: 10.1021/acsorginorgau.4c00032. eCollection 2024 Oct 2.
Carbonyl-containing 1,4,5-trisubstituted- and 1,4-disubstituted-1,2,3-triazoles are well-known for their wide range of applications in pharmaceutical and medicinal chemistry, but their high-yielding metal-free synthesis has always remained challenging, as no comprehensive protocol has been outlined to date. Owing to their structural and medicinal importance, herein, we synthesized various carbonyl-containing 1,4,5-trisubstituted- and 1,4-disubstituted-1,2,3-triazoles and unsymmetrical 4,5'-bitriazoles with high yields and chemo-/regioselectivity from the library of 2,4-diketoesters and azides in a sequential one-pot manner through the combination of organocatalytic enolization, in situ [3 + 2]-cycloaddition, and hydrolysis reactions. The commercial availability of the starting materials/catalysts, diverse substrate scope, performance in a one-pot manner, chemo-/regioselectivity of organo-click reaction, quick synthesis of unsymmetrical 4,5'-bitriazoles, a large number of synthetic applications, and numerous medicinal applications of carbonyl-containing 1,2,3-triazoles are the key attractions of this metal-free organo-click work.
含羰基的1,4,5-三取代和1,4-二取代-1,2,3-三唑因其在药物化学和医学化学中的广泛应用而闻名，但它们的高产无金属合成一直具有挑战性，因为迄今为止尚未概述全面的方案。由于它们的结构和药用重要性，在此，我们通过有机催化烯醇化、原位[3 + 2]环加成和水解反应的组合，以连续一锅法从2,4-二酮酯和叠氮化物库中高产率、化学/区域选择性地合成了各种含羰基的1,4,5-三取代和1,4-二取代-1,2,3-三唑以及不对称4,5'-双三唑。起始原料/催化剂的商业可用性、多样的底物范围、一锅法性能、有机点击反应的化学/区域选择性、不对称4,5'-双三唑的快速合成、大量的合成应用以及含羰基1,2,3-三唑的众多药用应用是这项无金属有机点击工作的关键吸引力。
