Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides

被引:122
|
作者
Brioche, Julien [1 ]
Meyer, Christophe [1 ]
Cossy, Janine [1 ]
机构
[1] PSL Res Univ, Lab Chim Organ, Inst Chem Biol & Innovat CBI, ESPCI ParisTech,CNRS UMR8231, F-75231 Paris 05, France
关键词
HIGHLY EFFICIENT SYNTHESIS; ONE-POT SYNTHESIS; FUNCTIONALIZED INDOLIZINES; CATALYZED CYCLIZATION; POLYSUBSTITUTED INDOLIZINES; CONVENIENT SYNTHESIS; C-C; ROUTE; HETEROCYCLES; NITROGEN;
D O I
10.1021/acs.orglett.5b01205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electron-deficient ynamides, possessing an ynoate or an ynone moiety, have been successfully involved for the first time in a 1,3-dipolar cycloaddition with stabilized pyridinium ylides. These reactions afford an efficient and general access toward a variety of substituted 2-aminoindolizines which can serve as useful precursors for the synthesis of other more complex nitrogen heterocycles.
引用
收藏
页码:2800 / 2803
页数:4
相关论文
共 50 条
  • [1] Synthesis of pyridinium ylides and simulation of their 1,3-dipolar cycloaddition mechanism
    Radzhabov, Maxim R.
    Tsyganov, Dmitriy V.
    Pivina, Tatyana S.
    Krayushkin, Mikhail M.
    Seeboth, Nicolas
    Ivanov, Sergey
    Salit, Anne-Frederique
    [J]. MENDELEEV COMMUNICATIONS, 2017, 27 (05) : 503 - 505
  • [2] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF DIAZOPYRAZOLINONES WITH ELECTRON-DEFICIENT DIPOLAROPHILES
    PADWA, A
    WOOLHOUSE, AD
    BLOUNT, JJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07): : 1069 - 1074
  • [3] REGIOSELECTIVITY ASSOCIATED WITH THE 1,3-DIPOLAR CYCLOADDITION OF NITRONES WITH ELECTRON-DEFICIENT DIPOLAROPHILES
    PADWA, A
    FISERA, L
    KOEHLER, KF
    RODRIGUEZ, A
    WONG, GSK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02): : 276 - 281
  • [4] ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS OF AZOMETHINE YLIDES WITH A CHIRAL ELECTRON-DEFICIENT OLEFINIC DIPOLAROPHILE
    KANEMASA, S
    YAMAMOTO, H
    [J]. TETRAHEDRON LETTERS, 1990, 31 (25) : 3633 - 3636
  • [5] 1,3-dipolar cycloaddition reactions between N-alkyl-3-hydroxy pyridinium halide and electron-deficient dipolarophiles
    [J]. Zhongshan Daxue Xuebao/Acta Scientiarum Natralium Universitatis Sunyatseni, 2002, 41 (03):
  • [6] 1,3-dipolar cycloaddition of azides with electron-deficient alkynes under mild condition in water
    Li, ZM
    Seo, TS
    Ju, JY
    [J]. TETRAHEDRON LETTERS, 2004, 45 (15) : 3143 - 3146
  • [7] Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides
    Day, Jonathan
    Uroos, Maliha
    Castledine, Richard A.
    Lewis, William
    McKeever-Abbas, Ben
    Dowden, James
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (38) : 6502 - 6509
  • [8] Diastereoselectivity in 1,3-dipolar cycloaddition reactions between indolic nitrones and electron-deficient alkenes
    Greci, L
    Tommasi, G
    Bruni, P
    Sgarabotto, P
    Righi, L
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (16) : 3147 - 3153
  • [9] 1,3-dipolar cycloaddition of Schiff bases and electron-deficient alkenes, catalyzed by α-amino acids
    Kudryavtsev, K. V.
    Zagulyaeva, A. A.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (03) : 378 - 387
  • [10] 1,3-dipolar cycloaddition of schriff bases and electron-deficient alkenes, catalyzed by α-Amino acids
    K. V. Kudryavtsev
    A. A. Zagulyaeva
    [J]. Russian Journal of Organic Chemistry, 2008, 44 : 378 - 387