Synthesis of potential fungicides based on N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides

被引:11
作者
Kolodziejczyk, Krzysztof [1 ]
Roiban, Gheorghe D. [2 ]
Schnuerch, Michael [1 ]
Mihovilovic, Marko D. [1 ]
Stanetty, Peter [1 ]
机构
[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
[2] Univ Babes Bolyai, Fac Chem & Chem Engn, Cluj Napoca 400028, Romania
来源
MONATSHEFTE FUR CHEMIE | 2009年 / 140卷 / 11期
关键词
ortho Lithiation; Fungicides; Organometallic compounds; Heterocycles; Suzuki reaction; DIRECTED METALATION REACTIONS; DERIVATIVES; ACIDS;
D O I
10.1007/s00706-009-0187-6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of novel N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides is presented starting from furan-3-carboxylic acid. Two complementary strategies to 2-aryl-3-furanamines with directed ortho lithiation, functionalization of the 2-position, and subsequent cross-coupling reaction as key steps were developed. Acylation of these intermediates with appropriate acid chlorides led finally to the target compounds.
引用
收藏
页码:1349 / 1359
页数:11
相关论文
共 33 条
[1]   3-ACYLAMINO FURANS [J].
CAMPBELL, MM ;
KAYE, AD ;
SAINSBURY, M .
TETRAHEDRON, 1982, 38 (18) :2783-2786
[2]   CHEMOSELECTIVE PROTECTION OF HETEROAROMATIC ALDEHYDES AS IMIDAZOLIDINE DERIVATIVES - PREPARATION OF 5-SUBSTITUTED FURAN-2-CARBOXALDEHYDE AND THIOPHENE-2-CARBOXALDEHYDE VIA METALLO-IMIDAZOLIDINE INTERMEDIATES [J].
CARPENTER, AJ ;
CHADWICK, DJ .
TETRAHEDRON, 1985, 41 (18) :3803-3812
[3]   GENERAL-ROUTE TO ANTHRAQUINONE NATURAL-PRODUCTS VIA DIRECTED METALATION OF N,N-DIETHYLBENZAMIDES [J].
DESILVA, SO ;
WATANABE, M ;
SNIECKUS, V .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4802-4808
[4]  
EBERLE M, 2002, Patent No. 0009482
[5]  
Graneto M.J., 1992, U.S. Patent, Patent No. [5093347, 5,093,347]
[6]  
GROSSMAN RB, 2000, ART WRITING REASONAB, P66
[7]  
Gschwend H.W., 1979, Organic React, V26, P1
[8]  
Haken P. T., 1969, Ger. Offen., Patent No. [DE 1914954, 1914954]
[9]  
HARRISON WA, 1973, Patent No. 3725427
[10]  
HUPPATZ JL, 1977, Patent No. 2701091