Intramolecular [2+2] cycloaddition of ketenimines with imines. Synthesis and chemical behaviour of azeto[2,1-b]quinazolines

被引:38
作者
Alajarin, M
Molina, P
Vidal, A
Tovar, F
机构
[1] Depto. de Quim. Orgánica, Facultad de Química, Campus de Espinardo
关键词
D O I
10.1016/S0040-4020(97)00855-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azeto[2,1-b]quinazolines 5 have been prepared by the novel intramolecular [2 + 2] cycloaddition reaction of ketenimines with imines. The applicability and limitations of the synthetic methodology, and explorations on the reactivity of compounds 5 are discussed. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:13449 / 13472
页数:24
相关论文
共 60 条
[31]   ANTITUMOR-ACTIVITY OF 5-ARYL-2,3-DIHYDROIMIDAZO[2,1-A]ISOQUINOLINES [J].
HOULIHAN, WJ ;
MUNDER, PG ;
HANDLEY, DA ;
CHEON, SH ;
PARRINO, VA .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (02) :234-240
[32]   Enantioselective total synthesis of irniine and bgugaine, bioactive 2-alkylpyrrolidine alkaloids [J].
Jossang, A ;
Melhaoui, A ;
Bodo, B .
HETEROCYCLES, 1996, 43 (04) :755-766
[33]   SYNTHESIS OF N-(TETRAZOL-5-YL)AZETIDINE-2-ONES [J].
KLICH, M ;
TEUTSCH, G .
TETRAHEDRON, 1986, 42 (10) :2677-2684
[34]  
KREUTZBERGER A, 1968, FORTSCHR ARZNEIMITT, V11, P356
[35]   Solvent and substituent effects in the periselectivity of the Staudinger reaction between ketenes and alpha,beta-unsaturated imines. A theoretical and experimental study [J].
Lecea, B ;
Arrastia, I ;
Arrieta, A ;
Roa, G ;
Lopez, X ;
Arriortua, MI ;
Ugalde, JM ;
Cossio, FP .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3070-3079
[36]   DIE ANWENDUNG DER NITRILIUMSALZE BEI DER SYNTHESE HETEROCYCLISCHER VERBINDUNGEN .3. DERIVATE DES 3.4-DIHYDRO-CHINAZOLINS [J].
LORATAMAYO, M ;
MADRONERO, R ;
MUNOZ, GG .
CHEMISCHE BERICHTE-RECUEIL, 1961, 94 (01) :208-216
[37]   VASICINONE - A BRONCHODILATOR PRINCIPLE FROM ADHATODA VASICA NES (NOACANTHACEAE) [J].
MEHTA, DR ;
NARAVANE, JS ;
DESAI, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :445-&
[38]  
MERCHAN F, 1982, SYNTHESIS-STUTTGART, P590
[39]   REACTIONS OF N-ALKYLIMINOCARBONIC ACID (O,O OR S,S)DIALKYL ESTERS .I. CYCLO ADDITIONS OF N-ALKYLIMINODITHIOCARBONIC ACID DIALKYL ESTERS WITH KETONES [J].
METZGER, C ;
WEGLER, R .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (03) :1120-&
[40]   SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - ONE-POT PREPARATION OF RIGID BICYCLIC GUANIDINES [J].
MOLINA, P ;
ALAJARIN, M ;
VIDAL, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1687-1695