Interceptive [4+1] Annulation of in Situ Generated 1,2-Diaza-1,3-dienes with Diazo Esters: Direct Access to Substituted Mono-, Bi-, and Tricyclic 4,5-Dihydropyrazoles

被引:76
作者
Attanasi, Orazio A. [1 ]
De Crescentini, Lucia [1 ]
Favi, Gianfranco [1 ]
Mantellini, Fabio [1 ]
Mantenuto, Serena [1 ]
Nicolini, Simona [1 ]
机构
[1] Univ Urbino Carlo Bo, Dept Biomol Sci, Sect Organ Chem & Organ Nat Cpds, I-61029 Urbino, Italy
关键词
CHLORIDE-CATALYZED REACTION; ELECTRON-RICH CARBENES; DIELS-ALDER REACTIONS; SULFUR YLIDES; CARBON-MONOXIDE; ENANTIOSELECTIVE SYNTHESIS; STRAIGHTFORWARD FORMATION; NECROPTOSIS INHIBITORS; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS;
D O I
10.1021/jo5016097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In situ derived acylic and cyclic 1,2-diaza-1,3dienes (DDs) were engaged in interceptive [4 + 1] annulation strategy with diazo esters (DEs). The catalytic activity of inexpensive copper(1) chloride allows the direct synthesis of mono-, hi-, and tricyclic 4,5-dihydropyrazole-5-carboxylic acid derivatives in a process that circumvents the use of an anhydrous and inert atmosphere.
引用
收藏
页码:8331 / 8338
页数:8
相关论文
共 76 条
  • [1] Discovery of novel phenoxyacetic acid derivatives as antimycobacterial agents
    Ali, Mohamed Ashraf
    Shaharyar, Mohammad
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) : 1896 - 1902
  • [2] Atlan V, 2000, SYNLETT, P489
  • [3] ATTANASI O, 1985, SYNTHESIS-STUTTGART, P157
  • [4] EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .31. SYNTHESIS OF NEW 3-CARBONYL-1-HETEROCYCLAMINOPYRROLES AND "3-CARBOXY-1-HETEROCYCLAMINOPYRROLES BY COPPER(II) CHLORIDE-CATALYZED REACTION OF HETEROCYCLIC AZOALKENES
    ATTANASI, O
    FILIPPONE, P
    MEI, A
    SERRAZANETTI, F
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (01) : 25 - 28
  • [5] A Novel Solvent-Free Approach to Imidazole Containing Nitrogen-Bridgehead Heterocycles
    Attanasi, Orazio A.
    Bianchi, Luca
    Campisi, Linda A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Mantellini, Fabio
    [J]. ORGANIC LETTERS, 2013, 15 (14) : 3646 - 3649
  • [6] Synthesis of Densely Functionalized 3a,4-Dihydro-1H-Pyrrolo[1,2-b]Pyrazoles via Base Mediated Domino Reaction of Vinyl Malononitriles with 1,2-Diaza-1,3-dienes
    Attanasi, Orazio A.
    Favi, Gianfranco
    Geronikaki, Athina
    Mantellini, Fabio
    Moscatelli, Giada
    Paparisva, Aliki
    [J]. ORGANIC LETTERS, 2013, 15 (11) : 2624 - 2627
  • [7] Powerful Approach to Heterocyclic Skeletal Diversity by Sequential Three-Component Reaction of Amines, Isothiocyanates, and 1,2-Diaza-1,3-dienes
    Attanasi, Orazio A.
    Bartoccini, Silvia
    Favi, Gianfranco
    Giorgi, Gianluca
    Perrulli, Francesca Romana
    Santeusanio, Stefania
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) : 1161 - 1167
  • [8] Cultivating the Passion to Build Heterocycles from 1,2-Diaza-1,3-dienes: the Force of Imagination
    Attanasi, Orazio A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Filippone, Paolino
    Mantellini, Fabio
    Perrulli, Francesca R.
    Santeusanio, Stefania
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) : 3109 - 3127
  • [9] REARRANGEMENT REACTIONS .3. SYNTHESES AND DIELS-ALDER REACTIONS OF 2-ALKYLAZO-SUBSTITUTED 1,3-BUTADIENES
    BANERT, K
    HAGEDORN, M
    [J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7331 - 7334
  • [10] Behr L.C., 1967, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, P1