Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

被引:7
|
作者
Narayanarao, Manjunatha [1 ]
Koodlur, Lokesh [2 ]
Revanasiddappa, Vijayakumar G. [3 ]
Gopal, Subramanya [2 ]
Kamila, Susmita [1 ]
机构
[1] Visvesvaraya Technol Univ, East Point Coll Engn & Technol, Bangalore 560049, Karnataka, India
[2] Vijayanagara Sri Krishnadevaraya Univ, Dept Studies & Res Che, Bellary 583105, India
[3] Tumkur Univ, Univ Coll Sci, Dept Chem, BH Rd, Tumakuru 572103, India
来源
关键词
L-proline; ninhydrin; sarcosine; spiropyrrolidine; 5-vinylindazole; 5-vinylindole; ONE-POT SYNTHESIS; 3-COMPONENT; DERIVATIVES; INHIBITORS;
D O I
10.3762/bjoc.12.288
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and stereospecific cyclic adducts.
引用
收藏
页码:2893 / 2897
页数:5
相关论文
共 50 条
  • [31] 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
  • [32] Synthesis of chlorins linked with pyrazoline by 1,3-dipolar diazomethane cycloaddition reaction
    Wang, Jin-Jun
    Li, Jia-Zhu
    Gryko, Daniel
    Shim, Young Key
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2006, 27 (07) : 1083 - 1085
  • [33] Synthesis of isoxazolines by 1,3-dipolar cycloaddition and their bioactivity
    Cheng, CS
    Li, ZN
    Su, JY
    Li, T
    Zhang, BY
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (11) : 1392 - 1397
  • [34] Microscale synthesis of a diphenylisoxazoline by a 1,3-dipolar cycloaddition
    Martin, WB
    Kateley, LJ
    Wiser, DC
    Brummond, CA
    JOURNAL OF CHEMICAL EDUCATION, 2002, 79 (02) : 225 - 227
  • [35] A Total Synthesis of (±)-Codeine by 1,3-Dipolar Cycloaddition
    Erhard, Thomas
    Ehrlich, Gunnar
    Metz, Peter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3892 - 3894
  • [37] One-pot, five-component 1,3-dipolar cycloaddition: A facile synthesis of spiropyrrolidine and spiropyrrolizidine derivatives
    Wen, Ren
    Cen, Lanqi
    Ma, Ying
    Wang, Jing
    Zhu, Songlei
    TETRAHEDRON LETTERS, 2018, 59 (17) : 1686 - 1690
  • [38] 1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: Synthesis of 2-hydroxy-1-deoxycastanospermine analogues
    Karanjule, NS
    Markad, SD
    Sharma, T
    Sabharwal, SG
    Puranik, VG
    Dhavale, DD
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04): : 1356 - 1363
  • [39] Multicomponent synthesis of highly substituted imidazolines via a silicon mediated 1,3-dipolar cycloaddition
    Peddibhotla, S
    Tepe, JJ
    SYNTHESIS-STUTTGART, 2003, (09): : 1433 - 1440
  • [40] 1,3-DIPOLAR CYCLOADDITION REACTION OF TRIFLUOROACETONITRILE WITH HETEROCYCLIC YLIDES
    KOBAYASHI, Y
    KUMADAKI, I
    KOBAYASHI, E
    HETEROCYCLES, 1981, 15 (02) : 1223 - 1225