Cycloaddition Reaction of 2-Vinylazetidines with Benzyne: A Facile Access to 1-Benzazocine Derivatives

被引：37

作者：

Aoki, Takashi ^{[1
]}

Koya, Shunsuke ^{[1
]}

Yamasaki, Ryu ^{[1
]}

Saito, Shinichi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Chem, Fac Sci, Shinjuku Ku, Tokyo 1628601, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

关键词：

RING EXPANSION; REGIOSELECTIVITY; CYCLIZATION; ANTAGONISTS; FR900482; ANALOGS; AGENTS;

D O I：

10.1021/ol3019924

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloaddition reaction of 2-vinylazetidines with benzyne proceeded smoothly without a catalyst, and various benzazocine derivatives were isolated in good to high yields. The scope of the reaction, as well as the reactions of other arynes, has been studied.

引用

页码：4506 / 4509

页数：4

共 20 条

[1] Sequential amino-claisen rearrangement/intramolecular 1,3-dipolar cycloaddition/reductive cleavage approach to the stereoselective synthesis of cis-4-hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines [J].

Ayala, Sandra Liliana Gomez ;

Stashenko, Elena ;

Palma, Alirio ;

Bahsas, Ali ;

Amaro-Luis, Juan Manuel .

SYNLETT, 2006, (14) :2275-2277

[2] LEWIS ACID-PROMOTED 3-AZA-COPE REARRANGEMENT OF N-ALKYL-N-ALLYLANILINES [J].

BEHOLZ, LG ;

STILLE, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5095-5100

[3] Synthesis and evaluation of CC-1065 and duocarmycin analogs incorporating the 1,2,3,4,11,11a-hexahydrocyclopropa[c]naphtho[2,1-b]azepin-6-one (CNA) alkylation subunit: Structural features that govern reactivity and reaction regioselectivity [J].

Boger, DL ;

Turnbull, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5849-5863

[4] The Benzyne Aza-Claisen Reaction [J].

Cant, Alastair A. ;

Bertrand, Guillaume H. V. ;

Henderson, Jaclyn L. ;

Roberts, Lee ;

Greaney, Michael F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5199-5202

[5] Ring expansions of 2-alkenylazetidinium salts - a new route to pyrrolidines and azepanes [J].

Couty, Francois ;

Durrat, Francois ;

Evano, Gwilherm ;

Marrot, Jerome .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (18) :4214-4223

[6] Ring Expansion of 2-Alkenyl Azetidines into Unsaturated Azocanes [J].

Drouillat, Bruno ;

Couty, Francois ;

Razafimahaleo, Vanessa .

SYNLETT, 2009, (19) :3182-3186

[7]

Fujiwara T, 2000, HETEROCYCLES, V52, P147

[8] Regioselectivity in aromatic Claisen rearrangements [J].

Gozzo, FC ;

Fernandes, SA ;

Rodrigues, DC ;

Eberlin, MN ;

Marsaioli, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5493-5499

[9] SMALL RINGS .29. SYNTHESIS AND RING EXPANSION OF VINYLAZETIDINES - A SYNTHESIS OF HYDROAZOCINES [J].

HASSNER, A ;

WIEGAND, N .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3652-3656

[10] FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS [J].

HIMESHIMA, Y ;

SONODA, T ;

KOBAYASHI, H .

CHEMISTRY LETTERS, 1983, (08) :1211-1214

← 1 2 →