One-Pot Preparation of (<i>NH</i>)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicarboxylic Acids
One-Pot Preparation of (<i>NH</i>)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicarboxylic Acids
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由联芳基二羧酸一锅法制备(<i>NH</i>)-菲啶酮和酰胺官能化[7]螺烯类分子
DOI：
10.1021/acs.joc.1c02769
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Furuta Takumi
中科院分区：
文献类型：
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作者：
Murai Takuya;Xing Yongning;Kurokawa Mayu;Kuribayashi Toshifumi;Nikaido Masanori;Elboray Elghareeb E.;Hamada Shohei;Kobayashi Yusuke;Sasamori Takahiro;Kawabata Takeo;Furuta Takumi
基于Curtius重排和随后的碱性水解，开发了联芳基二羧酸到（NH）-菲啶酮衍生物的一锅转化。该方法也适用于制备光学活性酰胺官能化的[7]螺烯类分子。此外，在带有硫族元素原子的底物的情况下，具有磷酸基团的氮杂[5]螺烯衍生物作为库尔修斯重排步骤的产物被分离。这些产品的立体结构，通过X-射线衍射分析，表明硫族元素键和磷族元素键的相互作用可能有助于他们的稳定。进一步研究了类螺烯分子的构型稳定性及其手性光学性质。
A one-pot transformation of biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives based on a Curtius rearrangement and subsequent basic hydrolysis was developed. This method is also applicable for the preparation of optically active amide-functionalized [7]helicene-like molecules. Furthermore, aza[5]helicene derivatives with a phosphate moiety were isolated as a product of the Curtius rearrangement step in the case of substrates that bear chalcogen atoms. The stereostructures of these products, revealed by X-ray diffraction analysis, suggested that chalcogen-bonding and pnictogen-bonding interactions might contribute to their stabilization. The configurational stability of the helicene-like molecules and their chiroptical properties were further investigated.