One-Pot Synthesis of Imidazole-4-Carboxylates by Microwave-Assisted 1,5-Electrocyclization of Azavinyl Azomethine Ylides

被引：47

作者：

Preti, Lisa ^{[1
]}

Attanasi, Orazio A. ^{[2
]}

Caselli, Emilia ^{[1
]}

Favi, Gianfranco ^{[2
]}

Ori, Claudia ^{[1
]}

Davoli, Paolo ^{[1
]}

Felluga, Fulvia ^{[3
]}

Prati, Fabio ^{[1
]}

机构：

[1] Univ Modena & Reggio Emilia, Dipartimento Chim, I-41100 Modena, Italy

[2] Univ Urbino Carlo Bo, Ist Chim Organ, I-61029 Urbino, Italy

[3] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 22期

基金：

美国国家卫生研究院;

关键词：

Azomethine ylides; Electrocyclic reactions; Microwave chemistry; Multicomponent reactions; Nitrogen heterocycles; ORGANIC-SYNTHESIS; SUBSTITUTED IMIDAZOLES; COPPER(II) CHLORIDE; EFFICIENT SYNTHESIS; METAL-IONS;

D O I：

10.1002/ejoc.201000434

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diversely functionalized imidazole-4-carboxylates were synthesized by microwave-assisted 1,5-eletrocyclization of 1,2-diaza-1,3-diene-derived azavinyl azomethine ylides 1,2-Diaza-1,3-dienes were treated with primary aliphatic or aromatic amines and subjected to microwave irradiation in the presence of aldehydes 3-Alkyl- and 3-arylimidazole-4-carboxylates were prepared in good yields through a one-pot multicomponent procedure. Modulation of the substituents at C-2, N-3, and C-5 was possible, and 2-unsubstituted Imidazoles were obtained when paraformaldehyde was used

引用

页码：4312 / 4320

页数：9

共 45 条

[1] Solvent-free thermal and microwave-assisted [3+2] cycloadditions between stabilized azomethine ylides and nitrostyrenes.: An experimental and theoretical study [J].

Arrieta, Ana ;

Otaegui, Dorleta ;

Zubia, Aizpea ;

Cossio, Fernando P. ;

Diaz-Ortiz, Angel ;

de la Hoz, Antonio ;

Herrero, M. Antonia ;

Prieto, Pilar ;

Foces-Foces, Concepcion ;

Pizarro, Jose L. ;

Arriortua, Maria I. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4313-4322

[2] Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes [J].

Attanas, Orazio A. ;

Favi, Gianfranco ;

Giorgi, Gianluca ;

Mantellini, Fabio ;

Karapetyan, Vahuni ;

Langer, Peter .

TETRAHEDRON, 2009, 65 (28) :5456-5461

[3] EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .30. SYNTHESIS OF NEW 3-CARBONYL-1-ALKOXYCARBONYLAMINOPYRROLES AND 3-CARBOXY-1-ALKOXYCARBONYLAMINOPYRROLES FROM REACTION CATALYZED BY COPPER(II) CHLORIDE OF ALKOXYCARBONYLAZOALKENES WITH BETA-DIKETONES AND BETA-KETOESTERS [J].

ATTANASI, O ;

FILIPPONE, P ;

MEI, A ;

SERRAZANETTI, F .

SYNTHETIC COMMUNICATIONS, 1986, 16 (03) :343-351

[4]

ATTANASI O, 1984, SYNTHESIS-STUTTGART, P671

[5] 1,2-Diaza-1,3-butadienes: just a nice class of compounds, or powerful tools in organic chemistry? Reviewing an experience [J].

Attanasi, OA ;

De Crescentini, L ;

Filippone, P ;

Mantellini, F ;

Santeusanio, S .

ARKIVOC, 2002, :274-292

[6] Azavinyl azomethine ylides from thermal ring opening of α-aziridinohydrazones:: Unprecedented 1,5-electrocyclization to imidazoles [J].

Attanasi, Orazio A. ;

Davoli, Paolo ;

Favi, Gianfranco ;

Filippone, Paolino ;

Forni, Arrigo ;

Moscatelli, Giada ;

Prati, Fabio .

ORGANIC LETTERS, 2007, 9 (17) :3461-3464

[7] Cultivating the Passion to Build Heterocycles from 1,2-Diaza-1,3-dienes: the Force of Imagination [J].

Attanasi, Orazio A. ;

De Crescentini, Lucia ;

Favi, Gianfranco ;

Filippone, Paolino ;

Mantellini, Fabio ;

Perrulli, Francesca R. ;

Santeusanio, Stefania .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) :3109-3127

[8] α-Aminoester-Derived Imidazoles by 1,5-Electrocyclization of Azavinyl Azomethine Ylides [J].

Attanasi, Orazio A. ;

Caselli, Emilia ;

Davoli, Paolo ;

Favi, Gianfranco ;

Mantellini, Fabio ;

Ori, Claudia ;

Prati, Fabio .

ORGANIC LETTERS, 2009, 11 (13) :2840-2843

[9] An Efficient One-Pot, Three-Component Synthesis of 5-Hydrazinoalkylidene Rhodanines from 1,2-Diaza-1,3-dienes [J].

Attanasi, Orazio A. ;

De Crescentini, Lucia ;

Favi, Gianfranco ;

Filippone, Paolino ;

Giorgi, Gianluca ;

Mantellini, Fabio ;

Moscatelli, Giada ;

Behalo, Mohamed S. .

ORGANIC LETTERS, 2009, 11 (11) :2265-2268

[10] Lewis Acid-Catalyzed Synthesis of Functionalized Pyrroles [J].

Attanasi, Orazio A. ;

Berretta, Stefano ;

De Crescentini, Lucia ;

Favi, Gianfranco ;

Giorgi, Gianluca ;

Mantellini, Fabio .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) :715-719

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