Reactivity of Functionalized N,S-Ketene Acetal: Regioselective Construction of Tetrahydrobenzo[b]pyran and Chromeno[2,3-b]quinoline Derivatives

被引：43

作者：

Li, Ming ^{[1
]}

Hou, Yan-Li ^{[1
]}

Wen, Li-Rong ^{[1
]}

Gong, Fu-Meng ^{[1
]}

机构：

[1] Qingdao Univ Sci & Technol, State Key Lab Base Ecochem Engn, Coll Chem & Mol Engn, Qingdao 266042, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 24期

基金：

中国国家自然科学基金;

关键词：

NAD(+)-DEPENDENT DNA-LIGASE; MULTICOMPONENT REACTIONS; COMBINATORIAL LIBRARIES; PRIVILEGED STRUCTURES; DOMINO REACTION; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; 1,4-DIHYDROPYRIDINES; FACILE; THIOAMIDES;

D O I：

10.1021/jo101902z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multi-component reactions (MCRs) and tandem [3 + 3] annulations of beta-benzoylthioacetanilides or beta-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethy1-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular SNAr in the presence of K2CO3 led to an unprecedented novel chromeno-[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.

引用

收藏

页码：8522 / 8532

页数：11

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