ortho-Lithiophenyl Isocyanide: A Versatile Precursor for 3H-Quinazolin-4-ones and 3H-Quinazolin-4-thiones

被引：73

作者：

Lygin, Alexander V. ^{[1
]}

de Meijere, Armin ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

ALPHA-METALATED ISOCYANIDES; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; LUOTONIN-A; COMBINATORIAL SYNTHESIS; PRACTICAL SYNTHESIS; INDOLE SYNTHESES; SIMPLE ALKALOIDS; DEOXYVASICINONE; DERIVATIVES;

D O I：

10.1021/ol802659m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

ortho-Lithiophenyl isocyanide has been generated from ortho-bromophenyl isocyanide and successfully employed toward the synthesis of 2-substituted phenyl isocyanides as well as 2,3-disubstituted 3H-quinazoline-4-ones and 3H-quinazolin-4-thiones.

引用

页码：389 / 392

页数：4

共 68 条

[31] Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst [J].

Kamijo, S ;

Kanazawa, C ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9260-9266

[32] Synthesis of imidazoles through the copper-catalyzed cross-cycloaddition between two different isocyanides [J].

Kanazawa, Chikashi ;

Kamijo, Shin ;

Yamamoto, Yoshinori .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10662-10663

[33]

KANEKO C, 1986, CHEM PHARM BULL, V34, P3672

[34] A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides [J].

Krasovskiy, A ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3333-3336

[35]

Krasovskiy A., 2004, ANGEW CHEM, V116, P3396, DOI DOI 10.1002/ANGE.200454084

[36] Versatile direct synthesis of oligosubstituted pyrroles by cycloaddition of α-metalated isocyanides to acetylenes [J].

Larionov, OV ;

de Meijere, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (35) :5664-5667

[37] A facile synthesis of simple alkaloids -: synthesis of 2,3-polymethylene-4(3H)-quinazolinones and related alkaloids [J].

Lee, ES ;

Park, JG ;

Jahng, Y .

TETRAHEDRON LETTERS, 2003, 44 (09) :1883-1886

[38] (2R,3S)-(+)- and (2S,3R)-(-)-Halofuginone lactate:: Synthesis, absolute configuration, and activity against Cryptosporidium parvum [J].

Linder, Michael R. ;

Heckeroth, Anja R. ;

Najdrowski, Michael ;

Daugschies, Arwid ;

Schollmeyer, Dieter ;

Miculka, Christian .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (15) :4140-4143

[39] Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation [J].

Liu, JF ;

Ye, P ;

Sprague, K ;

Sargent, K ;

Yohannes, D ;

Baldino, CM ;

Wilson, CJ ;

Ng, SC .

ORGANIC LETTERS, 2005, 7 (15) :3363-3366

[40] Nonpeptide glycoprotein IIb/IIIa inhibitors: Substituted quinazolinediones and quinazolinones as potent fibrinogen receptor antagonists [J].

Liverton, NJ ;

Armstrong, DJ ;

Claremon, DA ;

Remy, DC ;

Baldwin, JJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :483-486

← 1 2 3 4 5 6 7 →