A novel three-component reaction of anilines, formaldehyde and dimedone: simple synthesis of spirosubstituted piperidines

被引:46
作者
Kozlov, Nikolas G. [1 ]
Kadutskii, Aliaksei P. [1 ]
机构
[1] Natl Acad Sci Belarus, Inst Phys Organ Chem, Lab Organ Catalysis, Minsk 220072, BELARUS
关键词
beta-diketones; multicomponent reaction; mannich reaction; azaspiro compounds; piperidines;
D O I
10.1016/j.tetlet.2008.04.160
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component condensation of anilines with dimedone and formaldehyde leads to the formation of 3,5-dispirosubstituted piperidines. This simple reaction can serve as a convenient source of 3,5-disubstituted piperidines as well as polyfunctional 3-spirofused piperidines. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4560 / 4562
页数:3
相关论文
共 30 条
  • [1] Hydride-promoted ring expansion of 2-azaspiropyrrolinium salts: An approach towards the synthesis of (-)-nitramine
    Alonso, ER
    Tehrani, KA
    Boelens, M
    De Kimpe, N
    [J]. SYNLETT, 2005, (11) : 1726 - 1730
  • [2] Enantioselective synthesis of cis- and trans-3,5-disubstituted piperidines.: Synthesis of 20S- and 20R-dihydrocleavamine
    Amat, M
    Escolano, C
    Lozano, O
    Llor, N
    Bosch, J
    [J]. ORGANIC LETTERS, 2003, 5 (17) : 3139 - 3142
  • [3] New spiro-piperidines as 5-HT2B receptor antagonists
    Bienayme, Hugues
    Chene, Laurent
    Grisoni, Serge
    Grondin, Antonio
    Kaloun, Ei-Bachir
    Poigny, Stephane
    Rahali, Houcine
    Tam, Eric
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (18) : 4830 - 4833
  • [4] Chebanov V.A., 2004, CHEM HETEROCYCL COM+, V40, P475
  • [5] BIOLOGICALLY-ACTIVE ALKALOIDS FROM POISON FROGS (DENDROBATIDAE)
    DALY, JW
    [J]. JOURNAL OF TOXICOLOGY-TOXIN REVIEWS, 1982, 1 (01): : 33 - 86
  • [6] FURTHER CLASSIFICATION OF SKIN ALKALOIDS FROM NEOTROPICAL POISON FROGS (DENDROBATIDAE), WITH A GENERAL SURVEY OF TOXIC NOXIOUS SUBSTANCES IN THE AMPHIBIA
    DALY, JW
    MYERS, CW
    WHITTAKER, N
    [J]. TOXICON, 1987, 25 (10) : 1023 - 1095
  • [7] Alkaloids from frog skin: the discovery of epibatidine and the potential for developing novel non-opioid analgesics
    Daly, JW
    Garraffo, HM
    Spande, TF
    Decker, MW
    Sullivan, JP
    Williams, M
    [J]. NATURAL PRODUCT REPORTS, 2000, 17 (02) : 131 - 135
  • [8] DALY JW, 1982, PROGR CHEM ORGANIC N, P205
  • [9] An efficient chemoenzymatic access to chiral 3,7-diazabicyclo[3.3.1]nonane derivatives
    Danieli, B
    Lesma, G
    Passarella, D
    Silvani, A
    Viviani, N
    [J]. TETRAHEDRON, 1999, 55 (40) : 11871 - 11878
  • [10] Dzvinchuk I. B., 2001, CHEM HETEROCYCL COMP, V37, P506, DOI DOI 10.1023/A:1017668408493