Recyclization of 2-iminocoumarin-3-carbonitriles with 2-aminothiobenzamide: a new synthetic route to substituted 2-(2-iminocoumarin-3-yl)quinazoline-4(3H)-thiones

被引:5
作者
Shynkarenko, Pavlo E. [1 ]
Vlasov, Sergiy V. [1 ]
Kovalenko, Sergiy M. [1 ]
Chernykh, Valentin P. [1 ]
机构
[1] Natl Univ Pharm, Dept Organ Chem, UA-61002 Kharkov, Ukraine
关键词
iminocoumarin; quinazoline; thiobenzamide; rearrangement; recyclization; KNOEVENAGEL CONDENSATION; NUCLEOPHILIC-REAGENTS; ANTICANCER AGENTS; COUMARIN MOIETIES; QUINAZOLINE RING; HETEROCYCLES; DERIVATIVES; 2-IMINO-2H-1-BENZOPYRANS; CYCLIZATION; SYSTEMS;
D O I
10.1080/17415993.2010.509506
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of 2-aminothiobenzamide with either 2-iminocoumarin-3-carbonitrile or 2-iminocoumarin-3-thiocarboxamides has been studied. It has been established that in both cases, 2-(2-iminocoumarin-3-yl)quinazoline-4(3H)-thiones are formed as the result of a two-step procedure. The reactions of 2-(2-iminocoumarin-3-yl)quinazoline-4(3H)-thiones with arylamines and alkylating agents have been studied.
引用
收藏
页码:447 / 456
页数:10
相关论文
共 52 条
[1]  
Amine MS, 1998, INDIAN J HETEROCY CH, V7, P289
[2]   A novel and expedient approach to new heterocycles containing benzothiophene, benzothieno[2,3-d] pyrimidine and coumarin moieties [J].
Bilokin, YV ;
Vasylyev, MV ;
Branytska, OV ;
Kovalenko, SM ;
Chernykh, VP .
TETRAHEDRON, 1999, 55 (48) :13757-13766
[3]  
BLATTER HM, 1968, Patent No. 3403153
[4]   Parallel liquid-phase synthesis of benzopyrano[2,3-d]pyrimidine libraries [J].
Borisov, Alexander V. ;
Dzhavakhishvili, Sergey G. ;
Zhuravel, Irina O. ;
Kovalenko, Sergiy M. ;
Nikitchenko, Victor M. .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01) :5-8
[5]   Synthesis and anti-inflammatory activity of N-substituted 2-oxo-2H-1-benzopyran-3-carboxamides and their 2-iminoanalogues [J].
Bylov, IE ;
Vasylyev, MV ;
Bilokin, YV .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (11) :997-1001
[6]   KNOEVENAGEL CONDENSATION IN THE HETEROGENEOUS PHASE USING ALPO4-AL2O3 AS A NEW CATALYST [J].
CABELLO, JA ;
CAMPELO, JM ;
GARCIA, A ;
LUNA, D ;
MARINAS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5195-5197
[7]  
CHAURASIA MR, 1981, HETEROCYCLES, V16, P621
[8]   Uncatalysed Knoevenagel condensation in aqueous medium at room temperature [J].
Deb, ML ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2005, 46 (38) :6453-6456
[9]  
DOMINY BW, 1972, Patent No. 2134263
[10]   ACTIVATED NITRILES IN HETEROCYCLIC SYNTHESIS - NOVEL SYNTHESIS OF 5-IMINO-5H-[1]BENZOPYRANO[3,4-C]PYRIDINE-4(3H)-THIONES AND THEIR OXO ANALOGS [J].
ELGEMEIE, GEH ;
ELGHANDOUR, AHH .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (04) :1230-1232