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

页码：8522 / 8532

页数：11

共 69 条

[21] Thioamides as useful synthons in the synthesis of heterocycles [J].

Jagodzinski, TS .

CHEMICAL REVIEWS, 2003, 103 (01) :197-227

[22] Microwave Enabled Umpulong Mechanism Based Rapid and Efficient Four- and Six-Component Domino Formations of 2-(2′-Azaaryl)imidazoles and anti-1,2-Diarylethylbenzamides [J].

Jiang, Bo ;

Wang, Xiang ;

Shi, Feng ;

Tu, Shu-Jiang ;

Ai, Teng ;

Ballew, Austin ;

Li, Guigen .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9486-9489

[23] Four-Component Domino Reaction Leading to Multifunctionalized Quinazolines [J].

Jiang, Bo ;

Tu, Shu-Jiang ;

Kaur, Parminder ;

Wever, Walter ;

Li, Guigen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) :11660-+

[24] A clean one-pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media [J].

Jin, TS ;

Wang, AQ ;

Wang, X ;

Zhang, JS ;

Li, TS .

SYNLETT, 2004, (05) :871-873

[25] Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif [J].

Ko, Sung Kon ;

Jang, Hwan Jong ;

Kim, Eunha ;

Park, Seung Bum .

CHEMICAL COMMUNICATIONS, 2006, (28) :2962-2964

[26] Design, synthesis and antiproliferative activity of some new azapyranoxanthenone aminoderivatives [J].

Kolokythas, G ;

Pouli, N ;

Marakos, P ;

Pratsinis, H ;

Kletsas, D .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (01) :71-79

[27]

Konkoy C.S., 2001, Chem. Abstr., V134, Patent No. [00, 75123, 0075123]

[28] A new route to spiropyrrolidinyl-oxindole alkaloids via iodide ion induced rearrangement of [(N-aziridinomethylthio)methylene]-2-oxindoles [J].

Kumar, UKS ;

Ila, H ;

Junjappa, H .

ORGANIC LETTERS, 2001, 3 (26) :4193-4196

[29] Microwave-assisted combinatorial synthesis of hexa-substituted 1,4-dihydropyridines scaffolds using one-pot two-step multicomponent reaction followed by a S-alkylation [J].

Li, Ming ;

Zuo, Zhengquan ;

Wen, Lirong ;

Wang, Shuwen .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (03) :436-441

[30]

Lida F., 2007, TETRAHEDRON LETT, V48, P5379

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