Multiple cycloaromatization of novel aromatic enediynes bearing a triggering device on the terminal acetylene carbon

被引：33

作者：

Miyawaki, K ^{[1
]}

Kawano, T ^{[1
]}

Ueda, I ^{[1
]}

机构：

[1] Osaka Univ, Inst Sci & Ind Res, Osaka 5670047, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(98)01454-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic enediynes (1) bearing a triggering device on the terminal acetylene carbon undergo thermal cyclization at 25 degrees C to yield polyphenylene ring systems (6, 9, 13, and 15(16)) giving radical intermediates, dehydrobenzene monoradical (12) and didehydrobenzene biradicals (4 and 14) which may serve as a DNA-cleaving reagent. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6923 / 6926

页数：4

相关论文

共 7 条

[1] The chemistry of enediynes, enyne allenes and related compounds [J].

Grissom, JW ;

Gunawardena, GU ;

Klingberg, D ;

Huang, DH .

TETRAHEDRON, 1996, 52 (19) :6453-6518

[2]

MAIER ME, 1995, SYNLETT, P13

[3] Cycloaromatization of a non-conjugated polyenyne system: Synthesis of 5H-benzo[d]fluoreno[3,2-b]pyrans via diradicals generated from 1-[2-{4-(2-alkoxymethylphenyl)butan-1,3-diynyl}]phenylpentan-2,4-diyn-1-ols and trapping evidence for the 1,2-didehydrobenzene diradical [J].

Miyawaki, K ;

Suzuki, R ;

Kawano, T ;

Ueda, I .

TETRAHEDRON LETTERS, 1997, 38 (22) :3943-3946

[4] THERMAL GENERATION OF ALPHA,3-DEHYDROTOLUENE FROM (Z)-1,2,4-HEPTATRIEN-6-YNE [J].

MYERS, AG ;

KUO, EY ;

FINNEY, NS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8057-8059

[5]

NICOLAOU KC, 1995, MODERN ACETYLENE CHE, P203

[6] A surprising switch from the Myers-Saito cyclization to a novel biradical cyclization in enyne-allenes: Formal Diels-Alder and ene reactions with high synthetic potential [J].

Schmittel, M ;

Keller, M ;

Kiau, S ;

Strittmatter, M .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (05) :807-816

[7] Cascade radical cyclizations via biradicals generated from enediynes, enyne-allenes, and enyne-ketenes [J].

Wang, KK .

CHEMICAL REVIEWS, 1996, 96 (01) :207-222