Ugi-叠氮反应中的双功能砌块：探索新分子多样性的一般策略。
Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity.
机构信息
BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA.
出版信息
Org Biomol Chem. 2013 Sep 28;11(36):6036-46. doi: 10.1039/c3ob40900g.
Abstract
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.
摘要
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。
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