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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