An Unexpected Highly Stereoselective Bisaziridination of (E,E)-1,4-Dialkyl-2,3-dinitrobutadienes Followed by a Nitro Group Driven Ring Enlargement

被引：12

作者：

Ciogli, Alessia ^{[2
]}

Fioravanti, Stefania ^{[1
]}

Gasparrini, Francesco ^{[2
]}

Pellacani, Lucio ^{[1
]}

Rizzato, Egon ^{[3
]}

Spinelli, Domenico ^{[3
]}

Tardella, Paolo A. ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[2] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy

[3] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期

关键词：

SYNTHETIC EXPLOITATION; 1,4-DISUBSTITUTED 2,3-DINITRO-1,3-BUTADIENES; BIS-AZIRIDINE; IN-VITRO; 3,4-DINITROTHIOPHENE; ACCESS; DERIVATIVES; DILTIAZEM; EPOXIDES;

D O I：

10.1021/jo902112j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-2,2'-Dinitro-2,2'-biaziridines were obtained by a direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-1,3-butadienes under very mild conditions. The reactions occur with high stereoselectivity as shown by the enantioselective HPLC analyses performed on the crude mixtures. Ring enlargement to 3,3'-bi(1,2,4-oxadiazole) derivatives was easily obtained by a simple treatment with sodium iodide in DMSO, with an unforeseen regioselective aziridine C-C cleavage.

引用

页码：9314 / 9318

页数：5

共 51 条

[1] Base-induced heterochiral dimerization of an oxiranyl carbaldimine:: Stereoselective synthesis of a highly functionalized aziridine [J].

Alickmann, D ;

Fröhlich, R ;

Wurthwein, EU .

ORGANIC LETTERS, 2001, 3 (10) :1527-1530

[2] STUDIES OF ALLYLIC SUBSTITUTION CATALYZED BY A PALLADIUM COMPLEX OF A C-2-SYMMETRICAL BIS(AZIRIDINE) - PREPARATION AND NMR SPECTROSCOPIC INVESTIGATION OF A CHIRAL PI-ALLYL SPECIES [J].

ANDERSSON, PG ;

HARDEN, A ;

TANNER, D ;

NORRBY, PO .

CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (01) :12-16

[3]

Armaroli T, 2002, EUR J ORG CHEM, V2002, P1284, DOI 10.1002/1099-0690(200204)2002:7<1284::AID-EJOC1284>3.0.CO

[4]

2-X

[5]

Attanasi OA, 2003, SYNLETT, P995

[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] CS2CO3 OR CAO AS PROMOTERS OF ETHYL N-([(4-METHYLPHENYL)SULPHONYL]OXY)CARBAMATE IN AMINATION REACTIONS [J].

BARANI, M ;

FIORAVANTI, S ;

PELLACANI, L ;

TARDELLA, PA .

TETRAHEDRON, 1994, 50 (38) :11235-11238

[8] Access to 5,5′-diaryl substituted 4,5,4′,5′-tetrahydro[3,3′]bi-isoxazolyl 2,2′-dioxides, 4,5,4′,5′-tetrahydro[3,3′]bi-isoxazolyls and [3,3′]bi-isoxazolyls via an initial ring-opening of 3,4-dinitrothiophene [J].

Bianchi, L ;

Dell'Erba, C ;

Gasparrini, F ;

Novi, M ;

Petrillo, G ;

Sancassan, F ;

Tavani, C .

ARKIVOC, 2002, :142-158

[9] Nitrobutadienes from β-nitrothiophenes:: valuable building-blocks in the overall ring-opening/ring-closure protocol to homo- or hetero-cycles [J].

Bianchi, Lara ;

Dell'Erba, Carlo ;

Maccagno, Massimo ;

Morganti, Stefano ;

Petrillo, Giovanni ;

Rizzato, Egon ;

Sancassan, Fernando ;

Severi, Elda ;

Spinelli, Domenico ;

Tavani, Cinzia .

ARKIVOC, 2006, :169-185

[10] Neutral mono- and cationic bis-aziridine d6-metal complexes of the type [(π-arene)M(Az)Cl2] and [(π-arene)M(Az)2Cl]Cl (π-arene/M = η6-C6Me6/Ru; η5-C6Me6/Rh, Ir) [J].

Bobka, Roman ;

Roedel, J. Nicolas ;

Neumann, Bernd ;

Krinninger, Christoph ;

Mayer, Peter ;

Wunderlich, Stefan ;

Penger, Alexander ;

Lorenz, Ingo-Peter .

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2007, 633 (11-12) :1985-1994

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