Synthesis of substituted 3-(3-chloro-1H-pyrazol-5-yl)quinoxalin-2(1H)ones

被引：3

作者：

Steger, Stefan ^{[1
]}

Matuszczak, Barbara ^{[1
]}

机构：

[1] Univ Innsbruck, CCB, Inst Pharm Pharmaceut Chem, A-6020 Innsbruck, Austria

来源：

TETRAHEDRON | 2014年 / 70卷 / 38期

关键词：

Monomethoxy substituted 3-(3-chloro-1-H-pyrazol-5-yl)quinoxalin-2(1H)ones; 3,6-Dichloropyridazine-4-carboxamides; Pyridazine to pyrazole ring transformation; DERIVATIVES;

D O I：

10.1016/j.tet.2014.07.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic strategies to gain access to all four isomers of 3-(3-chloro-1H-pyrazol-5-yl)quinoxalin-2(1H) ones with monosubstituted benzo core (i.e., compounds 8a-d) are described. Preparation of these heterocyclic compounds succeeded starting from only two different substituted 2-nitroanilines (i.e., 3-methoxy- and 4-methoxy-2-nitroaniline) in three or five steps, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6763 / 6768

页数：6

共 18 条

[1] SELECTIVE REDUCTION OF AROMATIC NITRO-COMPOUNDS WITH STANNOUS CHLORIDE IN NON-ACIDIC AND NON-AQUEOUS MEDIUM [J].

BELLAMY, FD ;

OU, K .

TETRAHEDRON LETTERS, 1984, 25 (08) :839-842

[2] INTERMEDIATES IN THE SYNTHESIS OF CARBOXYL-C-14-LABELED 3-HYDROXYANTHRANILIC ACID [J].

CIERESZKO, LS ;

HANKES, LV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (09) :2500-2501

[3] An improved synthesis of N-Boc protected aryl amines [J].

Darnbrough, S ;

Mervic, M ;

Condon, SM ;

Burns, CJ .

SYNTHETIC COMMUNICATIONS, 2001, 31 (21) :3273-3280

[4]

Di Fabio R, 2000, CAN J CHEM, V78, P809

[5] Privileged structures: A useful concept for the rational design of new lead drug candidates [J].

Duarte, Carolina D. ;

Barreiro, Eliezer J. ;

Fraga, Carlos A. M. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (11) :1108-1119

[6] PYRIDAZINES .71. A NOVEL TYPE OF 1,2-DIAZINE -] 1,2-DIAZOLE RING CONTRACTION [J].

HEINISCH, G ;

MATUSZCZAK, B ;

MEREITER, K .

HETEROCYCLES, 1994, 38 (09) :2081-2089

[7] THE SYNTHESIS AND IONIZATION-CONSTANTS OF SOME DERIVATIVES OF 1-BIPHENYLENOL [J].

HINE, J ;

HAHN, S ;

MILES, DE ;

AHN, K .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5092-5096

[8] Synthesis, aggregation, and adsorption phenomena of shape-persistent macrocycles with extraannular polyalkyl substituents [J].

Höger, S ;

Bonrad, K ;

Mourran, A ;

Beginn, U ;

Möller, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5651-5659

[9]

Katritzky A.R., 1984, COMPREHENSIVE HETERO, V1-8

[10]

Katritzky A.R., 1996, COMPREHENSIVE HETERO, V1-9

← 1 2 →