Efficient synthesis of 2-imino-1,2-dihydroquinolines and 2-immothiochromenes via copper-catalyzed domino reaction

被引：64

作者：

Cui, Sun-Liang ^{[1
]}

Wang, Jing ^{[1
]}

Wang, Yan-Guang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

TETRAHEDRON | 2008年 / 64卷 / 03期

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

domino reaction; 2-imino-1,2-dihydroquinolines; 2-imino-thiochromenes; sulfonyl azides; alkynes;

D O I：

10.1016/j.tet.2007.11.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A domino approach to 2-imino-1,2-dihydroquinolines and 2-imino-thiochrornenes from sulfonyl azides, alkynes, and 2-acyl anilines or the potassium salt of 2-mercapto-benzaldehyde has been developed. This one-pot method is efficient and versatile. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：487 / 492

页数：6

共 35 条

[21] Pt(IV)-catalyzed cyclization of arene-alkyne substrates via C-H bond functionalization [J].

Pastine, SJ ;

Youn, SW ;

Sames, D .

TETRAHEDRON, 2003, 59 (45) :8859-8868

[22] Lewis acid-promoted carbon-carbon bond cleavage of aziridines: Divergent cycloaddition pathways of the derived ylides [J].

Pohlhaus, PD ;

Bowman, RK ;

Johnson, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2294-2295

[23] Structure-activity relationships in 1,4-benzodioxan-related compounds.: 7.: Selectivity of 4-phenylchroman analogues for α1-adrenoreceptor subtypes [J].

Quaglia, W ;

Pigini, M ;

Piergentili, A ;

Giannella, M ;

Gentili, F ;

Marucci, G ;

Carrieri, A ;

Carotti, A ;

Poggesi, E ;

Leonardi, A ;

Melchiorre, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (08) :1633-1643

[24] Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists [J].

Raitio, KH ;

Savinainen, JR ;

Vepsäläinen, J ;

Laitinen, JT ;

Poso, A ;

Järvinen, T ;

Nevalainen, T .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (06) :2022-2027

[25] Alkaloids from Galipea officinalis [J].

Rakotoson, JH ;

Fabre, N ;

Jacquemond-Collet, I ;

Hannedouche, S ;

Fourasté, I ;

Moulis, C .

PLANTA MEDICA, 1998, 64 (08) :762-763

[26] Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions [J].

Ranu, BC ;

Hajra, A ;

Dey, SS ;

Jana, U .

TETRAHEDRON, 2003, 59 (06) :813-819

[27] Asymmetric synthesis of 1,2-and 1,4-dihydroquinolines [J].

Rezgui, F ;

Mangeney, P ;

Alexakis, A .

TETRAHEDRON LETTERS, 1999, 40 (34) :6241-6244

[28]

Rogier D. J., 2001, Synthesis of dihydrobenzopyrans, dihydrobenzothiopyrans, and tetrahydroquinolines for the treatment of COX-2 mediated disorders, Patent No. [2001049675A1, 2001049675, WO 2001049675]

[29] A new polymer support silylene linking method for hindered hydroxyl-bearing systems [J].

Savin, KA ;

Woo, JCG ;

Danishefsky, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :4183-4186

[30]

Slcraup Z. H, 1880, CHEM BER, V13, P2086

← 1 2 3 4 →