吴沁, 王爽, 王灼钰, 黄顺桃, 黄超. 酸催化一锅法合成多芳环稠合[3.3.1]二氧杂壬烷衍生物[J]. 云南大学学报(自然科学版), 2022, 44(5): 1027-1033. doi: 10.7540/j.ynu.20210583
引用本文: 吴沁, 王爽, 王灼钰, 黄顺桃, 黄超. 酸催化一锅法合成多芳环稠合[3.3.1]二氧杂壬烷衍生物[J]. 云南大学学报(自然科学版), 2022, 44(5): 1027-1033. doi: 10.7540/j.ynu.20210583
WU Qin, WANG Shuang, WANG Zhuo-yu, HUANG Shun-tao, HUANG Chao. One-pot synthesis of multi-aromatic ring-fused [3.3.1] bicyclic compounds via acid-catalyzed[J]. Journal of Yunnan University: Natural Sciences Edition, 2022, 44(5): 1027-1033. DOI: 10.7540/j.ynu.20210583
Citation: WU Qin, WANG Shuang, WANG Zhuo-yu, HUANG Shun-tao, HUANG Chao. One-pot synthesis of multi-aromatic ring-fused [3.3.1] bicyclic compounds via acid-catalyzed[J]. Journal of Yunnan University: Natural Sciences Edition, 2022, 44(5): 1027-1033. DOI: 10.7540/j.ynu.20210583

酸催化一锅法合成多芳环稠合3.3.1二氧杂壬烷衍生物

One-pot synthesis of multi-aromatic ring-fused 3.3.1 bicyclic compounds via acid-catalyzed

  • 摘要: 报道了酸催化一锅法高效合成多芳环稠合3.3.1二氧杂壬烷衍生物的方法. 以2-羟基查尔酮化合物与2-萘酚为原料反应生成多环稠合氧杂环化合物,其反应机理有别于传统的迈克尔加成引起的环化过程,是酸催化2-羟基查尔酮脱水形成花青素中间体,再与2-萘酚发生亲电取代/分子内加成环化生成多环稠合氧杂环化合物的过程. 该反应原子经济性高,后处理简单. 以75%~92%产率生成多芳环稠合3.3.1二氧杂壬烷化合物,均经过1H NMR、13C NMR、HRMS和IR的表征鉴定.

     

    Abstract: This paper reports an acid-catalyzed tandem cyclization reaction for one-pot efficiently synthesize multi-aromatic ring-fused3.3.1dioxazonane compounds. This method used 2-hydroxychalcone compounds and 2-naphtholas as raw materials to synthesize polycyclic O-heterocyclic compounds. The reaction mechanism is different from the tandem process caused by the traditional Michael addition. It is a process in which 2-hydroxychalcone is dehydrated by acid to form anthocyanin intermediates, and then electrophilic substitution/intramolecular addition cyclization with 2-naphthol to form polycyclic fused oxygen-heterocyclic compounds. The reaction atom economy is high, and the post-processing is simple. This method can obtain molecular diversity multi-aromatic ring-fused3.3.1dioxazonane compounds with a yield of 75%−92%, all of which were characterized and identified by 1H NMR, 13C NMR, HRMS and IR.

     

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