Abstract

The possibility of functionalization of dipyrido[3,2-e:2′,3′-h]acenaphthene containing a quino[7,8-h]quinoline fragment and being a highly basic diazine analog of 1,8-bis(dimethylamino)naphthalene (“proton sponge”) has been studied for the first time. In addition to the pronounced tendency of the title compound to form associates with an intramolecular hydrogen bond of the NHN type (new examples with the participation of pyridine rings, including self-associates are shown) and its inertness to amination reactions of the pyridine rings, the naphthalene core at positions 5(8) and the CH₂CH₂ bridge (dehydrogenation) undergo chemical modifications under mild conditions, giving the corresponding acenaphthylenes. The latter can also be obtained in an unusual way by tele-elimination from 5,8-dibromodipyridoacenaphthene by reaction with neutral or anionic bases.

Beilstein J. Org. Chem. 2024, 20, 243–253. doi:10.3762/bjoc.20.24

摘要

含有喹啉[7,8- h ]喹啉片段的二吡啶并[3,2- e :2',3'- h ]苊的官能化可能性，并且是1,8-双（二​​甲氨基）的高碱性二嗪类似物首次研究了萘（“质子海绵”）。除了标题化合物与 NHN 型分子内氢键形成缔合体的明显倾向（显示了吡啶环参与的新例子，包括自缔合体）及其对吡啶环的胺化反应的惰性之外， 5(8)位的萘核和CH ₂ CH ₂桥（脱氢）在温和条件下进行化学修饰，得到相应的苊。后者也可以通过与中性或阴离子碱反应从5,8-二溴二吡啶并苊进行远程消除以不寻常的方式获得。

贝尔斯坦 J. 组织。化学。 2024, 20, 243–253。 doi:10.3762/bjoc.20.24