Azavinyl azomethine ylides from thermal ring opening of α-aziridinohydrazones:: Unprecedented 1,5-electrocyclization to imidazoles

被引：33

作者：

Attanasi, Orazio A.

Davoli, Paolo

Favi, Gianfranco

Filippone, Paolino

Forni, Arrigo

Moscatelli, Giada

Prati, Fabio

机构：

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

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

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 17期

关键词：

D O I：

10.1021/ol701522t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael-type addition of aziridinecarboxylates to 1,2-diaza-1,3-butadienes under solvent-free conditions (SFC) resulted in the formation of alpha-aziridinohydrazone adducts. In toluene under reflux, alpha-aziridinohydrazones gave imidazoles in moderate to good yields. Such a reactivity pattern is explained by 1,5-electrocyclization of azavinyl azomethine ylide generated through thermal ring opening of alpha-aziridinohydrazones.

引用

页码：3461 / 3464

页数：4

共 69 条

[1] [Anonymous], 1984, 1,3-Dipolar Cycloaddition Chemistry
[2] [Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
[3] [Anonymous], 2004, SCL SYNTH
[4] Improved synthesis of pyrroles and indoles via lewis acid-catalyzed Mukaiyama-Michael-type addition/heterocyclization of enolsilyl derivatives on 1,2-diaza-1,3-butadienes. Role of the catalyst in the reaction mechanism
Attanasi, Orazio A.
Favi, Gianfranco
Filippone, Paolino
Lillini, Samuele
Mantellini, Fabio
Spinelli, Domenico
Stenta, Marco
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (06) : 907 - 915
[5] DNA-directed alkylating agents. 7. Synthesis, DNA interaction, and antitumor activity of bis(hydroxymethyl)- and bis(carbamate)-substituted pyrrolizines and imidazoles
Atwell, GJ
Fan, JY
Tan, K
Denny, WA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) : 4744 - 4754
[6] Experimental and theoretical insights regarding the cycloaddition reaction of carbohydrate-based 1,2-diaza-1,3-butadienes and acrylonitrile.: A model case for the behavior of chiral azoalkenes and unsymmetric olefinst
Avalos, M
Babiano, R
Cintas, P
Clemente, FR
Gordillo, R
Jiménez, JL
Palacios, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) : 2241 - 2251
[7] A novel route to 2,3-pyrazol-1(5H)-ones via palladium-catalyzed carbonylation of 1,2-diaza-1,3-butadienes
Boeckman, RK
Reed, JE
Ge, P
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3651 - 3653
[8] A novel approach to 1-aryl-2-(p-tolylazo)alkenes from alkyl aryl ketones
Caposcialli, N
Dell'Erba, C
Novi, M
Petrillo, G
Tavani, C
[J]. TETRAHEDRON, 1998, 54 (20) : 5315 - 5324
[9] Cardillo G, 2003, ALDRICHIM ACTA, V36, P39
[10] NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - N-[(BENZYLOXY)BENZYL]IMIDAZOLES AND RELATED-COMPOUNDS AS POTENT ANTIHYPERTENSIVES
CARINI, DJ
DUNCIA, JV
JOHNSON, AL
CHIU, AT
PRICE, WA
WONG, PC
TIMMERMANS, PBMW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) : 1330 - 1336

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