Novel synthesis of N-methyl spiropyrrolidines by 1,3-dipolar cycloaddition reaction of azomethine ylides

被引:5
|
作者
Subramaniyan, G [1 ]
Jayashankaran, J [1 ]
Raghunathan, R [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
1,3-dipole; azomethine; ylide; spiropyrrolidines;
D O I
10.1080/00397910500182572
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel N-methyl spiropyrrolidines have been synthesized in good yield by the cycloaddition reaction of azomethine ylides generated by a decarboxylative route from sarcosine and paraformaldehyde with conformationally locked s-trans enone functionality present in the (E)-3-arylidene-4-chromanone as dipolarophiles. The structure of the title compound was established by spectroscopic techniques.
引用
下载
收藏
页码:2189 / 2193
页数:5
相关论文
共 50 条
  • [31] Direct synthesis of pyrroles via 1,3-dipolar cycloaddition of azomethine ylides with ynones
    Wang, Zheng
    Shi, Ying
    Luo, Xiaoyan
    Han, De-Man
    Deng, Wei-Ping
    NEW JOURNAL OF CHEMISTRY, 2013, 37 (06) : 1742 - 1745
  • [32] Diastereoselective 1,3-dipolar cycloaddition of cyclopropenes to acenaphthenequinone azomethine ylides
    Stepakov, Alexander, V
    Pronina, Yulia A.
    Filatov, Alexander S.
    Selivanov, Stanislav I.
    Kornev, Anton A.
    Kryukova, Mariya A.
    Ponyaev, Alexander I.
    Boitsov, Vitali M.
    TETRAHEDRON, 2024, 151
  • [33] 1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles
    Ryan, John H.
    ARKIVOC, 2015, : 160 - 183
  • [34] Unprecedented 1,3-dipolar cycloaddition of azomethine ylides to ester carbonyl
    Novikov, MS
    Voznyi, IV
    Khlebnikov, AF
    Kopf, J
    Kostikov, RR
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14): : 1628 - 1630
  • [35] Chiral oxazolines in 1,3-dipolar cycloaddition reactions of azomethine ylides
    Husinec, S
    Savic, V
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 1998, 63 (12) : 921 - 930
  • [36] DIASTEREOFACIAL SELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES
    DEPREZ, P
    ROUDEN, J
    CHIARONI, A
    RICHE, C
    ROYER, J
    HUSSON, HP
    TETRAHEDRON LETTERS, 1991, 32 (51) : 7531 - 7534
  • [37] 1,3-Dipolar cycloaddition reaction of two different azomethine ylides to C70
    郑大贵
    李玉良
    范楼珍
    李凤英
    李永舫
    朱道本
    Chinese Journal of Chemistry, 1998, (02) : 178 - 183
  • [38] 1,3-Dipolar cycloaddition reaction of two different azomethine ylides to C70
    Zheng, DG
    Li, YL
    Fan, LZ
    Li, FY
    Li, YF
    Zhu, DB
    CHINESE JOURNAL OF CHEMISTRY, 1998, 16 (02) : 178 - 183
  • [39] Direct construction of novel dispiro heterocycles through 1,3-dipolar cycloaddition of azomethine ylides
    Dandia, Anshu
    Jain, Anuj K.
    Bhati, Dharmendra S.
    TETRAHEDRON LETTERS, 2011, 52 (41) : 5333 - 5337
  • [40] 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