A Clean and Expedient Synthesis of Pyrido[1,4]oxazepino Spiropyrrolidines Through One-Pot, Three-Component [3+2] Cycloaddition Reaction

被引：2
作者：
Kathiravan, S. [1 ]
Babu, A. R. Suresh [1 ]
Raghunathan, R. [1 ]
机构：
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
来源：
SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 24期
关键词：
Azomethine ylide; Baylis-Hillman adducts; cycloaddition; pyrido[1; 4]-oxazepine; spiropyrrolidine; AZOMETHINE YLIDES; ALKALOIDS;
D O I：
10.1080/00397910903531730
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
One-pot three component synthesis of novel pyrido[1,4]-oxazepine fused spiropyrrolidines has been accomplished in good yields by 1,3-dipolar cycloaddition reaction of azomethine ylide, derived from paraformaldehyde and sarcosine with (E)-4-benzylidene-hexahydro-1H-pyrido[2,1-c][1,4]-oxazepine-3(7H)-one as dipolarophiles derived from Baylis-Hillman adducts. The effect of solvent on the [3+2]-cycloaddition reaction is also studied.
引用
收藏
页码：3721 / 3727
页数：7
相关论文
共 24 条
  • [1] Heteropolyacid-silica mediated [3+2] cycloaddition of azomethine ylides - a facile multicomponent one-pot synthesis of novel dispiroheterocycles
    Babu, A. R. Suresh
    Raghunathan, R.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (52) : 9221 - 9225
  • [2] ZrOCl2•8H2O mediated microwave induced [3+2] cycloaddition of azomethine ylides -: a facile one-pot synthesis of novel dispiroheterocycles
    Babu, A. R. Suresh
    Raghunathan, R.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (02) : 305 - 308
  • [3] Recent advances in the Baylis-Hillman reaction and applications
    Basavaiah, D
    Rao, AJ
    Satyanarayana, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
  • [4] Braekman JC, 1999, EUR J ORG CHEM, V1999, P1749
  • [5] Synthesis and biological evaluation of five-membered heterocycles fused to cyclopenta[c]thiophene as new antitumor agents
    Dallemagne, P
    Khanh, LP
    Alsaïdi, A
    Varlet, I
    Collot, V
    Paillet, M
    Bureau, R
    Rault, S
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) : 1161 - 1167
  • [6] ALKALOIDS FROM DENDROBATID FROGS - STRUCTURES OF 2 OMEGA-HYDROXY CONGENERS OF 3-BUTYL-5-PROPYLINDOLIZIDINE AND OCCURRENCE OF 2,5-DISUBSTITUTED PYRROLIDINES AND A 2,6-DISUBSTITUTED PIPERIDINE
    DALY, JW
    SPANDE, TF
    WHITTAKER, N
    HIGHET, RJ
    FEIGL, D
    NISHIMORI, N
    TOKUYAMA, T
    MYERS, CW
    [J]. JOURNAL OF NATURAL PRODUCTS, 1986, 49 (02): : 265 - 280
  • [7] Dapson in Heterocyclic Chemistry, Part IV: Synthesis of Some Novel Diphenylsulfones Containing Acetamide, Pyrrolidine, Piperazine, and Thiomorpholine Moieties as Antimicrobial and Antitumor Agents
    Ghorab, M. M.
    El Gaby, M. S. A.
    Amin, N. E.
    Taha, N. M. H.
    Shehab, M. A.
    Faker, I. M. I.
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) : 2929 - 2942
  • [8] DECARBOXYLATIVE TRANSAMINATION - MECHANISM AND APPLICATIONS TO THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS
    GRIGG, R
    THIANPATANAGUL, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) : 180 - 181
  • [9] 1,8-naphthyridines V. Novel N-substituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamides, as potent anti-inflammatory and/or analgesic agents completely devoid of acute gastrolesivity
    Grossi, G
    Di Braccio, M
    Roma, G
    Ballabeni, V
    Tognolini, M
    Barocelli, E
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (02) : 155 - 165
  • [10] Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum
    Guan, J
    Kyle, DE
    Gerena, L
    Zhang, QA
    Milhous, WK
    Lin, AJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (13) : 2741 - 2748
123