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

被引:64
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
Wu, Yao-Ting ;
Lin, Wei-Chih ;
Liu, Chia-Ju ;
Wu, Chuan-Yi .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) :1841-1849