Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds

被引:73
作者
Volmajer, J
Toplak, R
Leban, I
Le Marechal, AM
机构
[1] Univ Maribor, Fac Mech Engn, SLO-2000 Maribor, Slovenia
[2] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia
关键词
Knoevenagel condensation; iminocoumarins; coumarins; N-chlorination; N-chloro iminocoumarins; N-hydrazonocumarins;
D O I
10.1016/j.tet.2005.05.020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Knoevenagel reaction between 2-hydroxybenzaldehydes and active methylene compounds (malononitrile and ethyl cyanoacetate) produces iminocoumarins and/or coumarins. In order to study the reactivity of the prepared iminocoumarins, chlorination and reaction with N-nucleophiles were studied. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7012 / 7021
页数:10
相关论文
共 21 条
[1]   Synthesis and biological studies of some benzopyrano[2,3-c]pyrazole derivatives [J].
Abd Allah, OA .
FARMACO, 2000, 55 (9-10) :641-649
[2]  
BRUCE JM, 1971, J CHEM SOC C, P3749
[3]  
Brufola G, 1996, HETEROCYCLES, V43, P1257
[4]   BICYCLIC COMPOUNDS AS RING-CONSTRAINED INHIBITORS OF PROTEIN-TYROSINE KINASE-P56LCK [J].
BURKE, TR ;
LIM, B ;
MARQUEZ, VE ;
LI, ZH ;
BOLEN, JB ;
STEFANOVA, I ;
HORAK, ID .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (04) :425-432
[5]   PHASE-II STUDY OF COUMARIN AND CIMETIDINE IN PATIENTS WITH METASTATIC RENAL-CELL CARCINOMA [J].
DEXEUS, FH ;
LOGOTHETIS, CJ ;
SELLA, A ;
FITZ, K ;
AMATO, R ;
REUBEN, JM ;
DOZIER, N .
JOURNAL OF CLINICAL ONCOLOGY, 1990, 8 (02) :325-329
[6]   Heteroaromatization with 4-hydroxycoumarin part II: Synthesis of some new pyrano[2,3-d] pyrimidines, [1,2,4]triazolo[1,5-c]pyrimidines and pyrimido[1,6-b][1,2,4]triazine derivatives. [J].
El-Agrody, AM ;
El-Latif, MSA ;
El-Hady, NA ;
Fakery, AH ;
Bedair, AH .
MOLECULES, 2001, 6 (06) :519-527
[7]   Synthesis and biological evaluation of several 3-(coumarin-4-yl)tetrahydroisoxazole and 3-(coumarin-4-yl)dihydropyrazole derivatives [J].
Emmanuel-Giota, AA ;
Fylaktakidou, KC ;
Hadjipavlou-Litina, DJ ;
Litinas, KE ;
Nicolaides, DN .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) :717-722
[8]  
GREEN GR, 1996, COMPREHENSIVE HETERO, V5, P469
[9]  
Haugland R.P., 2002, Handbook of Fluorescent Probes and Research Products, V9th
[10]   POLYHYDROXYLATED 3-(N-PHENYL) CARBAMOYL-2-IMINOCHROMENE DERIVATIVES AS POTENT INHIBITORS OF TYROSINE KINASE P60(C-SRC) [J].
HUANG, CK ;
WU, FY ;
AI, YX .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (20) :2423-2428