A New Polynitrogen‐Heterocyclic Scaffold 2, 4, 6, 8‐Tetraazanoradamantane Skeleton: Synthesis and Conversion of Its Functionalities. Issue 7 (13th February 2023)

• Record Type: Journal Article
• Authors: Cai, Rongbin; Li, Bing; Hou, Tianjiao; Zhou, Qi; Liu, Yunzhi; Li, Huan; Gao, Yuan; Zhu, Longyi; Luo, Jun
• Is Part Of: Chinese journal of chemistry. Volume 41:Issue 7(2023)
• Page Start: 783
• Page End: 789
• Publication Date: 2023-02-13
• Subjects: Cage compounds -- Tetraazanoradamantane -- Multicomponent reactions -- Nitrogen heterocycles -- Condensation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202200659
• Languages: English
• ISSNs: 1001-604X

Abstract

Comprehensive Summary: 2, 4, 6, 8‐Tetraazanoradamantane skeleton is a unique rigid cage‐like organic structure that has not been established. In this article, a facile protocol to build all‐bridge‐position‐functionalized 2, 4, 6, 8‐tetraazanoradamantane skeleton by condensation of glyoxal, primary amines and disubstituted malondialdehydes, which were in situ generated from 2, 2‐dipropenyl‐1, 3‐dioxolane or 4, 4‐dimethoxyhepta‐2, 5‐diene via ozonation, is reported for the first time. A variety of primary amines are compatible with this process, and the corresponding 2, 4, 6, 8‐tetraalkyl‐2, 4, 6, 8‐tetraazanoradamantane‐9‐one ethylene or methyl ketals were achieved in 16%—58% yields. N ‐Benzyl group could be converted to other functionalities such as acetyl and nitro, which indicates the structural diversity of this scaffold. Abstract : A facile protocol of a "one‐pot" three‐step procedure to build the all‐bridge‐position‐functionalized 2, 4, 6, 8‐tetrazanoradamantane skeletons was developed. 23 samples were synthesized in 16%—58% yields, and the N ‐benzyl groups could be transferred to acetyl and nitro groups.