INTRAMOLECULAR ADDITION OF VINYL AND ARYL RADICALS TO OXIME ETHERS IN THE SYNTHESIS OF 5-MEMBERED, 6-MEMBERED AND 7-MEMBERED RING-SYSTEMS

被引：73

作者：

BOOTH, SE

JENKINS, PR

SWAIN, CJ

SWEENEY, JB

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,LEICS,ENGLAND

[2] MERCK SHARP & DOHME LTD,HARLOW CM20 2QR,ESSEX,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期

关键词：

D O I：

10.1039/p19940003499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxime ethers 2a-e have been cyclised with Bu(3)SnH to the alkoxyamino-3-methylidene-chromanes 3a-e. Seven-membered ring formation was observed when the oxime ethers 7a, b were converted into the dibenzo [b,e] oxepines 8a, b under similar conditions. 1-Methoxyaminoindanes 12a, b were produced from the cyclisation of the substrates 11a, b and the cis-fused cyclic products 15a, b and 18 were obtained from compounds 14a, b and 17, respectively.

引用

收藏

页码：3499 / 3508

页数：10

相关论文

共 29 条

[21] SYNTHESES OF BICYCLO[3.3.0]OCTANES VIA BIFURCATING RADICAL CYCLIZATION PATHWAYS [J].

NAGAI, M ;

LAZOR, J ;

WILCOX, CS .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3440-3442

[22] RADICAL CYCLIZATIONS OF OXIME ETHERS CONNECTED WITH ALDEHYDES OR KETONES - A NEW ENTRY TO CYCLIC AMINO-ALCOHOLS [J].

NAITO, T ;

TAJIRI, K ;

HARIMOTO, T ;

NINOMIYA, I ;

KIGUCHI, T .

TETRAHEDRON LETTERS, 1994, 35 (14) :2205-2206

[23] CARBOHYDRATES TO CARBOCYCLES - A SYNTHESIS OF (-)-ALPHA-PIPITZOL [J].

PAK, H ;

CANALDA, II ;

FRASERREID, B .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3009-3011

[24] RADICAL CYCLIZATIONS IN CONFORMATIONALLY RESTRAINED SYSTEMS - GENERATION OF THE CIS,CIS-HEXAHYDROPHENANTHRO(4,5-BCD)FURAN TETRACYCLE OF MORPHINE [J].

PARKER, KA ;

SPERO, DM ;

VANEPP, J .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4628-4630

[25] CASCADE RADICAL REACTIONS IN SYNTHESIS - A NEW RADICAL-MEDIATED DOUBLE-RING EXPANSION-CYCLIZATION PROCESS WITH OXIME ETHERS [J].

PATTENDEN, G ;

SCHULZ, DJ .

TETRAHEDRON LETTERS, 1993, 34 (42) :6787-6790

[26]

SIMPKINS NS, 1992, J CHEM SOC P1, P2417

[27]

STILL WC, 1978, J ORG CHEM, V43, P2932

[28] 5-MEMBERED VS 6-MEMBERED RING FORMATION IN THE VINYL RADICAL CYCLIZATION [J].

STORK, G ;

MOOK, R .

TETRAHEDRON LETTERS, 1986, 27 (38) :4529-4532

[29] VINYL RADICAL CYCLIZATIONS MEDIATED BY THE ADDITION OF STANNYL RADICALS TO TRIPLE BONDS [J].

STORK, G ;

MOOK, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2829-2831