文献类型：期刊文献

英文题名：Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4+3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita-Baylis-Hillman carbonates

作者：Wang, Kai-Kai[1,3];Ye, Jun-Wei[1];Jia, Jun[2];Li, Ya-Fei[1];Yao, Wei-Wei[1];Li, Lan-Xin[1];Zhao, Su-Miao[1];Xu, Yan[3];Chen, Rongxiang[1]

第一作者：Wang, Kai-Kai

通讯作者：Chen, RX[1];Xu, Y[2]

机构：[1]Xinxiang Univ, Sch Pharm, Xinxiang 453000, Peoples R China;[2]Jilin Prov Prod Qual Supervis & Inspection Inst, Changchun 130103, Peoples R China;[3]Xinxiang Med Univ, Henan Int Joint Lab Immun & Targeted Therapy Live, Xinxiang 453000, Henan, Peoples R China

第一机构：新乡学院

通讯机构：[1]corresponding author), Xinxiang Univ, Sch Pharm, Xinxiang 453000, Peoples R China;[2]corresponding author), Xinxiang Med Univ, Henan Int Joint Lab Immun & Targeted Therapy Live, Xinxiang 453000, Henan, Peoples R China.|[11071]新乡学院;

年份：2024

卷号：150

外文期刊名：TETRAHEDRON

收录：;Scopus(收录号：2-s2.0-85179066563);WOS:【SCI-EXPANDED(收录号:WOS:001139361500001)】；

基金：We are grateful for the financial support from the National Natural Science Foundation of China (21801214, K.-K.W.), the Program for Youth Backbone Teacher Training of Colleges and Universities in Henan Province, China (2021GGJS163, K.-K.W.) , the Higher Education Institution Key Research Project Plan of Henan Province (23A150044, K.-K. W. and 24A150033 R.X. Chen) and this work is supported by PhD research startup foundation of Xinxiang University (1366020133, K.-K. W.) .

语种：英文

外文关键词：spiro[indanone-benzazepine] scaffolds; [4+3] annulation; N-(o-chloromethyl)aryl amides; Ninhydrin-derived MBH carbonates; Aza-o-quinone methides

摘要：A [4 + 3] annulation of aza-o-quinone methides in situ-generated from N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita-Baylis-Hillman carbonates was realized under mild conditions. This protocol provides an efficient and practical approach for assembling a novel functionalized heterocyclic system incorporating benzazepines and spiro indane-1,3-dione motifs in high yields (up to 95 % yields) with good functionality tolerance. Moreover, the potential application of the methodology was further highlighted by several synthetic transformations. The structure of the typical product was straightforwardly demonstrated by X-ray crystallography.