[1]胡华安子,刘健,邱琳,等.钯催化连续亚胺/羰基化构建异喹啉酮四环化合物[J].常州大学学报(自然科学版),2024,36(04):8-15.[doi:10.3969/j.issn.2095-0411.2024.04.002]
　HU Huaanzi,LIU Jian,QIU Lin,et al.Palladium-catalyzed cascade imidoylation/carbonylation to construct isoquinolinone tetracyclic compounds[J].Journal of Changzhou University(Natural Science Edition),2024,36(04):8-15.[doi:10.3969/j.issn.2095-0411.2024.04.002]
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钯催化连续亚胺/羰基化构建异喹啉酮四环化合物()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
第36卷
期数:
2024年04期
页码:
8-15
栏目:
化学化工：有机合成专题
出版日期:
2024-07-28

文章信息/Info

Title:
Palladium-catalyzed cascade imidoylation/carbonylation to construct isoquinolinone tetracyclic compounds
文章编号:
2095-0411(2024)04-0008-08
作者:
胡华安子1; 刘健2; 邱琳1; 周舒文1; 崔朋飞1; 王程1; 蒋鹏举1; 王建浩1
(1.常州大学 药学院, 江苏 常州 213164; 2.常州恒邦药业有限公司, 江苏 常州 213001)
Author(s):
HU Huaanzi1;  LIU Jian2;  QIU Lin1;  ZHOU Shuwen1;  CUI Pengfei1;  WANG Cheng1;  JIANG Pengju1;  WANG Jianhao1
(1.School of Pharmacy, Changzhou University,Changzhou 213164, China; 2.Changzhou Hansoh Pharmaceutical Co., Ltd., Changzhou 213001, China)
关键词:
亚胺/羰基化;  异腈;  一氧化碳;  异喹啉酮
Keywords:
imidoylation/carbonylation;  isocyanide;  carbon monoxide;  isoquinolinone
分类号:
O 626.3
DOI:
10.3969/j.issn.2095-0411.2024.04.002
文献标志码:
A
摘要:
以1,3-双(2-碘代芳基)丙烷-2-胺类化合物作为底物,通过钯催化的异腈和一氧化碳的连续插入反应,构建异喹啉酮类骨架。经研究发现,与异腈互为等电子体的一氧化碳虽然在反应中过量的存在,但是异腈仍然优先迁移插入芳基Pd(Ⅱ)中间体,随后再进行一氧化碳的插入,最后还原消除得到相应的异喹啉酮类四环化合物。该反应条件温和,产率高达85%,产物经1H NMR, 13C NMR,高分辨质谱鉴定正确。
Abstract:
Using 1,3-bis(2-iodoaryl)propane-2-amines as substrates, a palladium-catalyzed sequential insertion of isocyanide and carbon monoxide to construct isoquinolinone skeletons has been developed. Compared with isoelectronic isocyanide counterparts, the migratory insertion of isocyanide to Ar-Pd(Ⅱ)is still prefer to carbon monoxide although carbon monoxide exists in large excess in the reaction. Followed by carbon monoxide insertion and finally reductive elimination, the corresponding isoquinolinone tetracyclic compounds were obtained. The reaction conditions were mild and the yields are up to 85%. The product was correctly identified by 1H NMR, 13C NMR and high-resolution mass spectrometry.

参考文献/References:

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备注/Memo

备注/Memo:
收稿日期: 2024-03-13。
作者简介: 胡华安子(1993—), 女, 江西南昌人, 博士, 讲师。通信联系人: 王建浩(1981—), E-mail: minuswan@cczu.edu.cn
更新日期/Last Update: 1900-01-01