Reactions of nitroso hetero-diels-alder cycloadducts with azides: Stereoselective formation of triazolines and aziridines

被引：38

作者：

Bodnar, Brian S.

Miller, Marvin J.

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

[2] Hans Knoell Inst, Leibniz Inst Nat Prod Res & Infect Biol, D-07745 Jena, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 10期

关键词：

D O I：

10.1021/jo0701987

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The addition of azides to acylnitroso hetero-Diels-Alder cycloadducts derived from cyclopentadiene affords exo-triazolines in excellent yield. The reaction is greatly affected by the level of alkene strain, while sterically demanding azides do not hinder the reaction. Conversion of the triazolines to aziridines is also described.

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页码：3929 / 3932

页数：4

相关论文

共 60 条

[1]

Alvarez SG, 1997, SYNTHESIS-STUTTGART, P413

[2] 1,3-DIPOLAR CYCLOADDITIONS TO STRAINED OLEFINS [J].

BECKER, KB ;

HOHERMUTH, MK .

HELVETICA CHIMICA ACTA, 1979, 62 (06) :2025-2036

[3] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[4] Lewis acid-promoted hetero Diels-Alder cycloaddition of α-acetoxynitroso dienophiles [J].

Calvet, G ;

Dussaussois, M ;

Blanchard, N ;

Kouklovsky, C .

ORGANIC LETTERS, 2004, 6 (14) :2449-2451

[5] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].

CICCHI, S ;

GOTI, A ;

BRANDI, A ;

GUARNA, A ;

DESARLO, F .

TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354

[6] REACTIONS OF TRANSIENT-C-NITROSOCARBONYL COMPOUNDS WITH DIENES, MONOOLEFINS, AND NUCLEOPHILES [J].

CORRIE, JET ;

KIRBY, GW ;

MACKINNON, JWM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04) :883-886

[7]

Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI DOI 10.1002/ANIE.196305651

[8]

HUNIG S, 1995, HETEROCYCLES, V40, P639

[9] First synthesis of 2′,3′-epimino-carbocydic nucleosides [J].

Ishikura, M ;

Murakami, A ;

Katagiri, N .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (03) :452-453

[10] A concise access to 6-azabicyclo[3.1.0] hexanes via high-pressure promoted cycloaddition reaction of azides to ABH [J].

Ishikura, M ;

Kudo, S ;

Hino, A ;

Ohnuki, N ;

Katagiri, N .

HETEROCYCLES, 2000, 53 (07) :1499-1504

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