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
来源：
SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 16期
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
收藏
页码：2189 / 2193
页数：5
相关论文
共 50 条
  • [1] Regioselective Synthesis of Novel Spiropyrrolidines and Spirothiapyrrolizidines Through Multicomponent 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides
    Liu, Hai
    Dou, Guolan
    Shi, Daqing
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (05): : 633 - 637
  • [2] A facile synthesis of ferrocene grafted N-methyl-spiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides
    Sureshbabu, A. R.
    Raghunathan, R.
    Satiskumar, B. K.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (23) : 2818 - 2821
  • [3] Synthesis of highly substituted spiropyrrolidines via 1,3-dipolar cycloaddition reaction of N-metalated azomethine ylides
    Subramaniyan, G
    Raghunathan, R
    [J]. TETRAHEDRON, 2001, 57 (14) : 2909 - 2913
  • [4] Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides
    Fang, Xin
    Wang, Chun-Jiang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (15) : 2591 - 2601
  • [5] Synthesis of novel spiroheterocyclic framework via the regioselective 1,3-dipolar cycloaddition reaction of azomethine ylides
    Hu, XF
    Feng, YQ
    [J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (13) : 1747 - 1752
  • [6] Synthesis of a novel dispiroheterocyclic framework via the regioselective 1,3-dipolar cycloaddition reaction of azomethine ylides
    Babu, A. R. Suresh
    Raghunathan, R.
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) : 451 - 458
  • [7] Expedient Synthesis of Novel Ferrocenyl Spiropyrrolidines Through 1,3-Dipolar Cycloaddition Reaction
    Kathiravan, S.
    Raghunathan, R.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (04) : 906 - 910
  • [8] Synthesis of Spirocyclic Amines by 1,3-Dipolar Cycloaddition of Azomethine Ylides and Azomethine Imines
    Choi, Anthony
    Castle, Jemma
    Saruengkhanphasit, Rungroj
    Coldham, Iain
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (08): : 1273 - 1278
  • [9] 1,3-Dipolar cycloaddition of fluorinated azomethine ylides at the C=N bond
    Novikov, MS
    Khlebnikov, AR
    Egarmin, MA
    Kopf, J
    Kostikov, RR
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (10) : 1493 - 1499
  • [10] PYRROLIDINES BY 1,3-DIPOLAR CYCLOADDITION OF CONJUGATED AZOMETHINE YLIDES
    COLDHAM, I
    COLLIS, AJ
    MOULD, RJ
    ROBINSON, DE
    [J]. SYNTHESIS-STUTTGART, 1995, (09): : 1147 - &
12345