A novel route to 2,3-pyrazol-1(5H)-ones via palladium-catalyzed carbonylation of 1,2-diaza-1,3-butadienes

被引:63
|
作者
Boeckman, RK [1 ]
Reed, JE [1 ]
Ge, P [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
关键词
D O I
10.1021/ol016565x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel Pd(0)-catalyzed carbonylation of both isolable 1,2-diaza-1,3-butadienes and those generated in situ by extrusion of SO2 and CO2 from heterocyclic precursors is described. The reaction proceeds at room temperature to 110 degreesC under 1-2 atm of CO to afford 2,3-pyrazol-1(5H)-ones in good to excellent yields. The effect of catalyst structure and stability on the carbonylation reaction is evaluated.
引用
收藏
页码:3651 / 3653
页数:3
相关论文
共 50 条
  • [1] On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes
    Attanasi, Orazio A.
    Favi, Gianfranco
    Filippone, Paolino
    Forzato, Cristina
    Giorgi, Gianluca
    Morganti, Stefano
    Nitti, Patrizia
    Pitacco, Giuliana
    Rizzato, Egon
    Spinelli, Domenico
    Valentin, Ennio
    TETRAHEDRON, 2006, 62 (26) : 6420 - 6434
  • [2] Straightforward entry into 5-hydroxy-1-aminopyrrolines and the corresponding pyrroles from 1,2-diaza-1,3-butadienes
    Attanasi, OA
    De Crescentini, L
    Favi, G
    Filippone, P
    Mantellini, F
    Santeusanio, S
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23): : 8178 - 8181
  • [3] Reactions of 1,2-diaza-1,3-butadienes with propargyl alcohol as an approach to novel bi-heterocyclic systems
    De Crescentini, L.
    Perrulli, F. R.
    Favi, G.
    Santeusanio, S.
    Giorgi, G.
    Attanasi, O. A.
    Mantellini, F.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (37) : 8674 - 8678
  • [4] Azo-coupling decarboxylation reaction of α-carboxy ketene dithioacetals in water -: A new route to 1,2-diaza-1,3-butadienes
    Xu Xian-Xiu
    Wang Mang
    Liu Qun
    Pan Ling
    Zhao Yu-Long
    CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (10) : 1431 - 1434
  • [5] One-pot synthesis of spiro pyrroloimidazoles and 2-arylimidazoles from 1,2-diaza-1,3-butadienes and arylamidines
    Attanasi, Orazio A.
    Giorgi, Gianluca
    Favi, Glanfranco
    Filippone, Paolino
    Lillini, Samuele
    Perrulli, Francesca R.
    Santeisanio, Stefania
    SYNLETT, 2007, (11) : 1691 - 1694
  • [6] Access to new 2-oxofuro[2,3-b]pyrroles and 2-methylenepyrroles through the reaction of 1,2-diaza-1,3-butadienes and γ-ketoesters
    Attanasi, OA
    De Crescentini, L
    Favi, G
    Filippone, P
    Mantellini, F
    Santeusanio, S
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08): : 2686 - 2692
  • [7] Solid-phase synthesis of 4-triphenylphosphoranylidene-4,5-dihydropyrazol-5-ones, 4-aminocarbonyl-pyrroles, 4-methoxy-1H-pyrazol-5(2H)-ones and 2-thiazolin-4-ones from polymer-bound 1,2-diaza-1,3-butadienes
    Attanasi, OA
    De Crescentini, L
    Filippone, P
    Mantellini, F
    Tietze, LF
    TETRAHEDRON, 2001, 57 (27) : 5855 - 5863
  • [8] Reaction of some 1,2-diaza-1,3-butadienes with activated methine compounds.: A straightforward entry to 1,4-dihydropyridazine, pyridazine, and 4,5(4H,5H)-cyclopropylpyrazole derivatives
    Attanasi, OA
    Filippone, P
    Fiorucci, C
    Foresti, E
    Mantellini, F
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26): : 9880 - 9887
  • [9] Aspects of the chemistry of functionalized 1-phenylpyrazoles available from 1,2-diaza-1,3-butadienes and 2-phenylazo-1,3-dicarbonyl compounds
    Attanasi, OA
    Filippone, P
    Fiorucci, C
    Mantellini, F
    TETRAHEDRON LETTERS, 1999, 40 (20) : 3891 - 3894
  • [10] Palladium-catalyzed trimerizations of terminal arylalkynes: Synthesis of 1,3-diaryl-2-arylethynyl-1,3-butadienes
    Wu, Yao-Ting
    Lin, Wei-Chih
    Liu, Chia-Ju
    Wu, Chuan-Yi
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) : 1841 - 1849