Synthesis of medium ring heterocycles using an intramolecular Heck reaction

被引：88

作者：

Arnold, LA

Luo, WC

Guy, RK

机构：

[1] Univ Calif San Francisco, Dept Pharmaceut Chem, San Francisco, CA 94143 USA

[2] Univ Calif San Francisco, Dept Cellular & Mol Pharmacol, San Francisco, CA 94143 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 17期

关键词：

D O I：

10.1021/ol0487884

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.

引用

页码：3005 / 3007

页数：3

共 23 条

[11] Gürtler C, 1999, CHEM-EUR J, V5, P3107, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3107::AID-CHEM3107>3.0.CO
[12] 2-#
[13] Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand
Hartwig, JF
Kawatsura, M
Hauck, SI
Shaughnessy, KH
Alcazar-Roman, LM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) : 5575 - 5580
[14] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .4.
HEGEDUS, LS
SESTRICK, MR
MICHAELSON, ET
HARRINGTON, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) : 4141 - 4146
[15] On the efficiency of tetraalkylammonium salts in Heck type reactions
Jeffery, T
[J]. TETRAHEDRON, 1996, 52 (30) : 10113 - 10130
[16] DIBENZ[B,F]AZEPINES AND RELATED RING-SYSTEMS
KRICKA, LJ
LEDWITH, A
[J]. CHEMICAL REVIEWS, 1974, 74 (01) : 101 - 123
[17] Formal total synthesis of the PKC inhibitor, balanol: preparation of the fully protected benzophenone fragment
Laursen, B
Denieul, MP
Skrydstrup, T
[J]. TETRAHEDRON, 2002, 58 (11) : 2231 - 2238
[18] LINK JT, 2002, ORG REACTIONS, V60, P157, DOI DOI 10.1002/0471264180.0R060.02
[19] Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[20] 2-U

← 1 2 3 →