A Facile Regioselective Synthesis of Novel Spiroacenaphthene Pyrroloisoquinolines Through 1,3-Dipolar Cycloaddition Reactions

被引:6
作者
Sarrafi, Yaghoub [1 ]
Asghari, Asieh [1 ]
Hamzehloueian, Mahshid [2 ]
Alimohammadi, Kamal [3 ]
Sadatshahabi, Marzieh [1 ]
机构
[1] Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
[2] Islamic Azad Univ, Jouybar Branch, Dept Chem, Jouybar, Iran
[3] Univ Farhangian, Dr Shariati Branch, Dept Chem, Sari, Iran
关键词
1,3-dipolar cycloaddition; azomethine ylide; 1,5]-H shift; spiroacenaphthene pyrroloisoquinolines; AZOMETHINE YLIDE CYCLOADDITION; CONSTRUCTION; AZIRIDINES;
D O I
10.5935/0103-5053.20130245
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient one-pot three-component procedure for the synthesis of novel spiroacenaphthene pyrroloisoquinolines with high regioselectivity is described. These compounds were prepared from 1,3-dipolar cycloaddition of an azomethine ylide generated from acenaphthenequinone and 1,2,3,4-tetrahydroisoquinoline via [1,5]-H shift, with chalcone and nitrostyrene derivatives as dipolarophiles. The structure and stereochemistry of the cycloadducts have been established by single crystal X-ray structure and spectroscopic techniques.
引用
收藏
页码:1957 / +
页数:64
相关论文
共 50 条
  • [31] 1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles
    Ryan, John H.
    ARKIVOC, 2015, : 160 - 183
  • [32] Synthesis of new spirooxindole derivatives through 1,3-dipolar cycloaddition of azomethine ylides and their antitubercular activity
    Rouatbi, Fadwa
    Askri, Moheddine
    Nana, Frederic
    Kirsch, Gilbert
    Sriram, Dharmarajan
    Yogeeswari, Perumal
    TETRAHEDRON LETTERS, 2016, 57 (02) : 163 - 167
  • [33] Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles
    Arumugam, Natarajan
    Kumar, Raju Suresh
    Almansour, Abdulrahman I.
    Perumal, Subbu
    CURRENT ORGANIC CHEMISTRY, 2013, 17 (18) : 1929 - 1956
  • [34] A facile synthesis of novel endo-selective polycyclic spiropyrrolidine oxindoles via 1,3-dipolar cycloaddition of α,γ-dialkylallenoate esters
    Wang, Yingwei
    Chen, Yuanwei
    TETRAHEDRON LETTERS, 2017, 58 (16) : 1545 - 1547
  • [35] A facile synthesis of novel dispiroindano thiazolo [2,3-b] benzo[h]quinazoline pyrrolidines through 1,3-dipolar cycloaddition reaction
    Kathiravan, S.
    Raghunathan, R.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (07): : 1117 - 1119
  • [36] An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides
    Babu, A. R. Suresh
    Raghunathan, R.
    TETRAHEDRON LETTERS, 2008, 49 (31) : 4618 - 4620
  • [37] Stereoselective synthesis of PEGylated azoles via 1,3-dipolar cycloaddition
    Kazakova, Angelina, V
    Rubicheva, Lyubov G.
    Konev, Alexander S.
    Khlebnikov, Alexander F.
    TETRAHEDRON, 2021, 77
  • [38] Synthesis of Spirocyclic Pyrrolizidineoxyindoles with a Furotropylidene Fragment by 1,3-Dipolar Cycloaddition
    A. V. Tkachuk
    S. V. Kurbatov
    O. N. Burov
    M. E. Kletskii
    P. G. Morozov
    V. I. Minkin
    Chemistry of Heterocyclic Compounds, 2014, 50 : 26 - 34
  • [39] Synthesis of Spirocyclic Pyrrolizidineoxyindoles with a Furotropylidene Fragment by 1,3-Dipolar Cycloaddition
    Tkachuk, A. V.
    Kurbatov, S. V.
    Burov, O. N.
    Kletskii, M. E.
    Morozov, P. G.
    Minkin, V. I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (01) : 26 - 34
  • [40] An expedient regio and diastereoselective synthesis of novel spiropyrrolidinylindenoquinoxalines via 1,3-dipolar cycloaddition reaction
    Reddy, Marri Sameer
    Chowhan, L. Raju
    Kumar, Nandigama Satish
    Ramesh, Pambala
    Mukkamala, Saratchandra Babu
    TETRAHEDRON LETTERS, 2018, 59 (14) : 1366 - 1371