Marcaccini Stefano, Torroba Tomás
Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, Via della Lastruccia, 13, I-50019 Sesto Fiorentino, Italy.
Nat Protoc. 2007;2(3):632-9. doi: 10.1038/nprot.2007.71.
This protocol describes a procedure for the Ugi four-component condensation. It describes the general mechanism as well as the effects of the nature of the components on the Ugi reaction. It also describes the effects of the reaction conditions on the reaction, along with special procedures and workup. The experimental procedure is exemplified by a description of the preparation of N-cyclohexyl 2-[N-(2-chloroacetyl)-N-(4-chlorobenzyl)]amino-2-(4-chlorophenyl)acetamide, a typical Ugi product, that is subsequently used for the synthesis of a 2,5-diketopiperazine, an example of an important type of pharmaceutical compound. The experimental procedure is then extended to the synthesis of a 1,5-disubstituted tetrazole via Ugi four-component condensation. The protocol describes the preparation and characterization of the new 1-cyclohexyl-5-(1-phenylamino-2-methyl)propyltetrazole. The total time for the synthesis and isolation of the two example reactions in parallel is 3 d.
本方案描述了Ugi四组分缩合反应的步骤。它阐述了一般反应机理以及各组分性质对Ugi反应的影响。还描述了反应条件对该反应的影响，以及特殊步骤和后处理方法。通过制备典型的Ugi产物N-环己基2-[N-(2-氯乙酰基)-N-(4-氯苄基)]氨基-2-(4-氯苯基)乙酰胺对实验步骤进行了举例说明，该产物随后用于合成一种2,5-二酮哌嗪，这是一种重要类型的药物化合物的实例。然后将实验步骤扩展到通过Ugi四组分缩合反应合成1,5-二取代四唑。该方案描述了新型1-环己基-5-(1-苯基氨基-2-甲基)丙基四唑的制备和表征。并行合成和分离这两个示例反应的总时间为3天。
