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.
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收藏
页码:13449 / 13472
页数:24
相关论文
共 60 条
[1]   Intramolecular [2+2] cycloaddition of ketenimines with imines [J].
Alajarin, M ;
Molina, P ;
Vidal, A .
TETRAHEDRON LETTERS, 1996, 37 (49) :8945-8948
[2]   CHROMIUM CARBENE-MEDIATED SYNTHESIS OF 4-OXO BETA-LACTAMS (MALONIMIDES) AND MALONIC-ACID DERIVATIVES [J].
ALCAIDE, B ;
DOMINGUEZ, G ;
PLUMET, J ;
SIERRA, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :447-451
[3]   IMINODITHIOCARBONATES AS FORMALDEHYDE IMINE EQUIVALENTS - SEQUENTIAL 2-STEP APPROACH TO LI UNSUBSTITUTED BETA-LACTAMS THROUGH CHROMIUM(0) CARBENE PHOTOCYCLOADDITION NICKEL BORIDE DESULFURIZATION [J].
ALCAIDE, B ;
CASARRUBIOS, L ;
DOMINGUEZ, G ;
SIERRA, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7934-7936
[4]   The intramolecular aldol condensation route to fused bi- and tricyclic beta-lactams [J].
Alcaide, B ;
Polanco, C ;
Saez, E ;
Sierra, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7125-7132
[5]   The asymmetric synthesis of 2,3-benzocarbapenems by intramolecular aryl radical cyclizations [J].
Alcaide, B ;
Moreno, AM ;
RodriguezVicente, A ;
Sierra, MA .
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2203-2206
[6]   CARBENES .20. IMINOCARBENE-KETENIMINE REARRANGEMENT [J].
ARNOLD, B ;
REGITZ, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (04) :320-320
[7]   Studies on lactams .99. Fused tricyclic beta-lactams via intramolecular aryl radical cyclization [J].
Banik, BK ;
Subbaraju, GV ;
Manhas, MS ;
Bose, AK .
TETRAHEDRON LETTERS, 1996, 37 (09) :1363-1366
[8]  
BARI SS, 1992, SYNTHESIS-STUTTGART, P439
[9]   REACTIVITY AND SELECTIVITY OF N-VINYLIC LAMBDA-5-PHOSPHAZENES TOWARDS ELECTROPHILES - SYNTHESIS OF 2-AZA-1,3-DIENES [J].
BARLUENGA, J ;
FERRERO, M ;
PALACIOS, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08) :2193-2197
[10]   Highly functionalised monocyclic and bicyclic beta-lactams via alkene metathesis [J].
Barrett, AGM ;
Baugh, SPD ;
Gibson, VC ;
Giles, MR ;
Marshall, EL ;
Procopiou, PA .
CHEMICAL COMMUNICATIONS, 1997, (02) :155-156