BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA.
Org Biomol Chem. 2013 Sep 28;11(36):6036-46. doi: 10.1039/c3ob40900g.
1,5-Disubstituted tetrazoles are an important drug-like scaffold known for their ability to mimic the cis-amide bond conformation. The scaffold is readily accessible via substitution of the carboxylic acid component of the Ugi multi-component reaction (MCR) with TMSN3 in what is herein denoted the Ugi-azide reaction. This full paper presents a concise, novel, general strategy to access a plethora of new heterocylic scaffolds utilizing tethered aldo/keto-acids/esters in the Ugi-azide reaction followed by a ring closing event that generates novel highly complex bis-heterocyclic lactam-tetrazoles.
1,5-取代四唑是一种重要的类药骨架，因其能够模拟顺式酰胺键构象而闻名。该骨架可通过 Ugi 多组分反应（MCR）中羧酸组分与 TMSN3 的取代来制备，在此称为 Ugi-叠氮反应。本文提出了一种简洁、新颖、通用的策略，通过 Ugi-叠氮反应中连接的醛/酮酸/酯，随后进行环合反应，生成新型高度复杂的双杂环内酰胺-四唑，从而获得大量新的杂环骨架。
