Facile construction of the all-bridge-position-functionalized 2, 4, 6, 8-tetraazaadamantane skeleton and conversion of its N-functionalities. Issue 14 (1st June 2022)

• Record Type: Journal Article
• Authors: Cai, Rongbin; Zhou, Qi; Hou, Tianjiao; Li, Bing; Liu, Yunzhi; Li, Huan; Gao, Yuan; Zhu, Longyi; Luo, Jun
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 14(2022)
• Page Start: 3684
• Page End: 3691
• Publication Date: 2022-06-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00427e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An unusual protocol of a "one-pot" three-step strategy to build the 2, 4, 6, 8-tetraazaadamantane skeleton was developed. 17 products were obtained in 19–46% yields, and the N -benzyl groups were transferred to nitroso, acetyl, benzoyl and nitro groups. Abstract : The 2, 4, 6, 8-tetraazaadamantane skeleton is a novel rigid symmetric cage-like organic structure and the construction of this kind of scaffold is a long-standing challenge. In this article, an unusual protocol of a "one-pot" three-step strategy to build the special all-bridge-position-functionalized tetraazaadamantane skeletons from 2, 2-dipropenyl-1, 3-dioxolane via ozonation, hydrogenation with 5% Pd/BaSO4, and condensation of the in situ generated dial intermediate with primary amines is reported for the first time. Different primary amines are compatible with this process, and the corresponding 2, 4, 6, 8-tetraalkyl-2, 4, 6, 8-tetraazaadamantane-9, 10-dione bis(ethylene ketals) were achieved in 19–46% yields. The conversion of the N -benzyl group to some other functionalities such as acetyl, benzoyl, nitroso and nitro was also investigated.