含氨基的1,4,6,10-四氮杂金刚烷（TAADs）：硼螯合物和主客体配合物的合成与形成

1,4,6,10-Tetraazaadamantanes (TAADs) with -amino groups: synthesis and formation of boron chelates and host-guest complexes.

作者信息

Semakin Artem N, Golovanov Ivan S, Nelyubina Yulia V, Sukhorukov Alexey Yu

机构信息

Laboratory of organic and metal-organic nitrogen-oxygen systems, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, Russian Federation.

Center for molecular composition studies, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str. 28, Moscow, Russian Federation.

出版信息

Beilstein J Org Chem. 2022 Oct 11;18:1424-1434. doi: 10.3762/bjoc.18.148. eCollection 2022.

DOI:10.3762/bjoc.18.148

PMID:36300009

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9577388/

Abstract

A synthetic route to 1,4,6,10-tetraazaadamantanes (TAADs) bearing free and protected amino groups at the bridge -atoms has been developed via intramolecular cyclotrimerization of C=N units in the corresponding tris(hydrazonoalkyl)amines. In a similar fashion, unsymmetrically substituted TAADs having both amino and hydroxy groups at the bridge -atoms were prepared via a hitherto unknown co-trimerization of oxime and hydrazone groups. The use of -TAAD derivatives as potential ligands and receptors was showcased through forming boron chelates and host-guest complexes with water and simple alcohols.

摘要

通过相应的三（腙基烷基）胺中C=N单元的分子内环三聚反应，开发了一种在桥原子上带有游离和保护氨基的1,4,6,10-四氮杂金刚烷（TAADs）的合成路线。以类似的方式，通过肟基和腙基迄今未知的共三聚反应，制备了在桥原子上同时具有氨基和羟基的不对称取代TAADs。通过与水和简单醇形成硼螯合物和主客体配合物，展示了-TAAD衍生物作为潜在配体和受体的用途。