Modification of Pyrrolo[2,1-a]isoquinolines and Polysubstituted Pyrroles via Methylenation with Acetyl Chloride and Dimethylsulfoxide

被引：10
|
作者：
Li, Wan-Zhen [1 ]
Zhang, Wei [1 ]
Chen, Xiao-Hui [1 ]
Wang, Zhao-Dong [2 ]
Cui, Hai-Lei [1 ]
机构：
[1] Chongqing Univ Arts & Sci, Lab Asymmetr Synth, Chongqing 402160, Peoples R China
[2] Chongqing Univ Arts & Sci, Coll Chem & Environm Engn, Chongqing Key Lab Environm Mat & Remediat Technol, Chongqing 402160, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 17期
基金：
中国国家自然科学基金;
关键词：
DIMETHYL-SULFOXIDE; REGIOSELECTIVE SYNTHESIS; CONVENIENT ACCESS; DMSO; OXIDATION; INDOLES; REAGENT; ACID; FORMYLATION; CYCLIZATION;
D O I：
10.1021/acs.joc.2c01090
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient synthesis of methylene-bridged pyrrolo[2,1-a]isoquinolines has been developed. Treatment of pyrroloisoquinolines with acetyl chloride and dimethylsulfoxide (DMSO) at ambient temperature afforded bispyrroloisoquinolylmethanes in 17-85% yields. This reaction system can also be expanded to the synthesis of bispyrrolylmethanes (34-94% yields). Easy chemical transformation of methylene-bridged pyrroloisoquinoline provided an unsymmetric acid and amide possessing a privileged framework.
引用
收藏
页码：11491 / 11502
页数：12
相关论文
共 50 条
  • [21] Enantioselective intramolecular α-amidoalkylation reaction in the synthesis of pyrrolo[2,1-a]isoquinolines
    Gomez-SanJuan, Asier
    Sotomayor, Nuria
    Lete, Esther
    TETRAHEDRON LETTERS, 2012, 53 (17) : 2157 - 2159
  • [22] Modification of Pyrrolo[2,1-a]isoquinolines through Iron-Catalyzed Aminomethylenation with Amines and Dimethyl Sulfoxide
    Chen, Xiao-Hui
    Cui, Hai-Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (31)
  • [23] Copper-Catalyzed Tandem Synthesis of Indolo-, Pyrrolo[2,1-a]isoquinolines, Naphthyridines and Bisindolo/Pyrrolo[2,1-a]isoquinolines via Hydroamination of ortho-Haloarylalkynes Followed by C-2 Arylation
    Verma, Akhilesh K.
    Jha, Rajeev R.
    Chaudhary, Ritu
    Tiwari, Rakesh K.
    Reddy, Kotla Siva K.
    Danodia, Abhinandan
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18): : 8191 - 8205
  • [24] Electronic spectra of pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-f]phenanthridines
    Mikhailovskii, A.G.
    Shklyaev, V.S.
    Chemistry of Heterocyclic Compounds, 1995, 31 (05): : 573 - 576
  • [25] Controllable Diastereodivergent Synthesis of Pyrrolo[2,1-a]isoquinolines via Catalytic Intramolecular Acylsulfenylation of Activated Alkenes
    Liu, Wei
    Du, Shan-Tao
    Wang, Shu-Yue
    Liao, Wei-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09): : 4829 - 4839
  • [26] Green production and antioxidant activity study of new pyrrolo[2,1-a]isoquinolines
    Amiri, Somayeh Soleimani
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (11) : 4057 - 4069
  • [27] NHC-Mediated Synthesis of Pyrrolo[2,1-a]isoquinolines and Their Photophysical Investigations
    Krishnan, Jagadeesh
    Vedhanarayanan, Balaraman
    Sasidhar, B. S.
    Varughese, Sunil
    Nair, Vijay
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (06) : 623 - 627
  • [28] Synthesis of pyrrolo[2,1-a]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline
    Yavari, Issa
    Piltan, Mohammad
    Moradi, Loghman
    TETRAHEDRON, 2009, 65 (10) : 2067 - 2071
  • [29] Iron-catalyzed dimerization of pyrrolo[2,1-a]isoquinolines and pyrrolo [1,2-a]quinolines
    Huang, Xiang
    Li, Wan-Zhen
    Pei, Shu-Chen
    Cui, Hai -Lei
    TETRAHEDRON LETTERS, 2023, 126
  • [30] Facile Access to Benzothiazole-containing Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Nitrogen Ylides
    Dawood, Kamal M.
    Ragab, Eman A.
    Khedr, Nabila A.
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2009, 56 (06) : 1180 - 1185
12345