Regioselective Synthesis of Tetrasubstituted Pyrroles by 1,3-Dipolar Cycloaddition and Spontaneous Decarboxylation

被引：58
|
作者：
Kim, Yongju [1 ]
Kim, Jonghoon [1 ]
Park, Seung Bum [1 ]
机构：
[1] Seoul Natl Univ, Dept Chem, Seoul 151747, South Korea
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 01期
关键词：
STEREOSELECTIVE-SYNTHESIS; MUNCHNONES; DERIVATIVES; ALKYNES; IMINES; POTENT;
D O I：
10.1021/ol8022193
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2h)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).
引用
收藏
页码：17 / 20
页数：4
相关论文
共 50 条
  • [21] Regioselective Synthesis of Mono- and Dispiropyrazoline Derivatives via 1,3-dipolar Cycloaddition with Nitrilimines
    Rouatbi, Fadwa
    Mhiri, Chourouk
    Askri, Moheddine
    Knorr, Michael
    Rousselin, Yoann
    Kubicki, Marek M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) : 1152 - 1160
  • [22] Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition
    Zhang, Bolong
    White, Jonathan M.
    Jones, David J.
    Wong, Wallace W. H.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (42) : 10505 - 10510
  • [23] A facile and regioselective synthesis of rimonabant through an enamine-directed 1,3-dipolar cycloaddition
    Donohue, Sean R.
    Halldin, Christer
    Pike, Victor W.
    TETRAHEDRON LETTERS, 2008, 49 (17) : 2789 - 2791
  • [24] A Facile Regioselective Synthesis of Novel Spiroacenaphthene Pyrroloisoquinolines Through 1,3-Dipolar Cycloaddition Reactions
    Sarrafi, Yaghoub
    Asghari, Asieh
    Hamzehloueian, Mahshid
    Alimohammadi, Kamal
    Sadatshahabi, Marzieh
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2013, 24 (12) : 1957 - +
  • [25] Regioselective synthesis of novel spiroindane-1,3-diones through 1,3-dipolar cycloaddition reactions
    Sarrafi, Yaghoub
    Hamzehlouian, Mahshid
    Alimohammadi, Kamal
    Khavasi, Hamid Reza
    TETRAHEDRON LETTERS, 2010, 51 (36) : 4734 - 4737
  • [26] Synthesis of Heteroaryl-Substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Unsymmetrical Munchnones and Nitrovinylheterocycles
    Lopchuk, Justin M.
    Song, Mia
    Butler, Blythe
    Gribble, Gordon W.
    SYNTHESIS-STUTTGART, 2015, 47 (18): : 2776 - 2780
  • [27] SYNTHESIS OF NOVEL SPIROHETEROCYCLES THROUGH 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE YLIDES WITH TRIARYLIDENEACETYLACETONE THROUGH DECARBOXYLATION
    Murugan, Ramalingam
    Raghunathan, R.
    Narayanan, S. Sriman
    SYNTHETIC COMMUNICATIONS, 2010, 40 (21) : 3135 - 3151
  • [28] Tri- and Tetrasubstituted N-Phthalimidoaziridines in 1,3-Dipolar Cycloaddition Reactions
    Ushkov, Alexander V.
    Kuznetsov, Mikhail A.
    Linden, Anthony
    Heimgartner, Heinz
    HELVETICA CHIMICA ACTA, 2010, 93 (05) : 847 - 862
  • [29] Molecularly imprinted nanoreactors for regioselective Huisgen 1,3-dipolar cycloaddition reaction
    Zhang, Huiqi
    Piacham, Theeraphon
    Drew, Mark
    Patek, Marcel
    Mosbach, Klaus
    Ye, Lei
    Journal of the American Chemical Society, 2006, 128 (13): : 4178 - 4179
  • [30] Molecularly imprinted nanoreactors for regioselective huisgen 1,3-dipolar cycloaddition reaction
    Zhang, QH
    Piacham, T
    Drew, M
    Patek, M
    Mosbach, K
    Ye, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) : 4178 - 4179
12345