Gas-phase pyrolysis in organic synthesis: rapid green synthesis of 4-quinolinones

被引:44
作者
Al-Awadi, Nouria A. [1 ]
Abdethamid, Ismail Abdelshafy [1 ]
Al-Etaibi, Alya M. [1 ]
Elnagdi, Mohamed Hilmy [1 ]
机构
[1] Kuwait Univ, Fac Sci, Dept Chem, Safat 13060, Kuwait
关键词
meldrum's acid; pyrolysis; 4-quinolinones;
D O I
10.1055/s-2007-985573
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed ketene-amine interniediate.
引用
收藏
页码:2205 / 2208
页数:4
相关论文
共 21 条
[1]   Gas-phase thermolysis of 1-acylnaphtho[1,8-de][1,2,3]triazines.: Interesting direct routes towards condensed naphtho[1,8-de] heterocyclic ring systems [J].
Al-Awadi, H ;
Ibrahim, MR ;
Dib, HH ;
Al-Awadi, NA ;
Ibrahim, YA .
TETRAHEDRON, 2005, 61 (44) :10507-10513
[2]   Gas-phase thermolysis of benzotriazole derivatives. Part 3: Kinetic and mechanistic evidence for biradical intermediates in pyrolysis of aroylbenzotriazoles and related compounds [J].
Al-Awadi, NA ;
George, BJ ;
Dib, HH ;
Ibrahim, MR ;
Ibrahim, YA ;
El-Dusouqui, OME .
TETRAHEDRON, 2005, 61 (34) :8257-8263
[3]   Efficient synthesis of 3-aroylcinnolines from aryl methyl ketones [J].
Al-Awadi, NA ;
Elnagdi, MH ;
Ibrahim, YA ;
Kaul, K ;
Kumar, A .
TETRAHEDRON, 2001, 57 (08) :1609-1614
[4]   SYNTHESIS OF 4(1H)-QUINOLONES BY THERMOLYSIS OF ARYLAMINOMETHYLENE MELDRUM ACID-DERIVATIVES [J].
CASSIS, R ;
TAPIA, R ;
VALDERRAMA, JA .
SYNTHETIC COMMUNICATIONS, 1985, 15 (02) :125-133
[5]  
CHEN BC, 1987, SYNTHESIS-STUTTGART, P482
[6]  
CZUBA W, 1980, POL J CHEM, V54, P1573
[7]  
GRIERA R, 1997, EUR J MED CHEM, P547
[8]   CYCLIZATION OF AMINE-ACETYLENE DIESTER ADDUCTS - A MODIFICATION OF CONRAD-LIMPACH METHOD (1) [J].
HEINDEL, ND ;
BRODOF, TA ;
KOGELSCHATZ, JE .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (02) :222-+
[9]  
HIARI YM, 2006, HETEROCYCLES, V68, P1163
[10]   3-HYDROXYPYRROLES AND 1H-PYRROL-3(2H)-ONES .1. FORMATION AND X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF 1-CYCLOHEXYL-2,2-PENTAMETHYLENE-1H-PYRROL-3(2H)-ONE [J].
HICKSON, CL ;
KEITH, EM ;
MARTIN, JC ;
MCNAB, H ;
MONAHAN, LC ;
WALKINSHAW, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1465-1469