REACTION OF SCHIFF-BASES OF 1-TETRALONE WITH ACID-CHLORIDES - STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS SPIROANNULATED WITH THE TETRAHYDRONAPHTHALENE RING-SYSTEM

被引：5
作者：
BOGDANOWICZSZWED, K
KRASODOMSKA, M
机构：
[1] Department of Organic Chemistry, Jagiellonian University, Kraków
来源：
MONATSHEFTE FUR CHEMIE | 1994年 / 125卷 / 11期
关键词：
ACID CHLORIDES; CYCLOADDITION; BETA-LACTAMS; SCHIFF BASES;
D O I：
10.1007/BF00813811
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Arylimines of 1-tetralone (1) react with various substituted acetyl chlorides (2) in the presence of triethylamine yielding p-lactams spiroannulated with tetrahydronaphthalene (3). The stereochemistry of the products has been determined by NMR methods. Reactions of imines 1 with acid chlorides 2 were proved to be highly stereoselective.
引用
收藏
页码：1247 / 1258
页数：12
相关论文
共 21 条
[1]  
AOYAMA T, 1981, CHEM PHARM BULL, V29, P3249
[2]   N,N-DIMETHYLCHLOROSULFITEMETHANIMINIUM CHLORIDE (SOCL2-DMF) A VERSATILE DEHYDRATING REAGENT [J].
ARRIETA, A ;
AIZPURUA, JM ;
PALOMO, C .
TETRAHEDRON LETTERS, 1984, 25 (31) :3365-3368
[3]   REAGENTS AND SYNTHETIC METHODS .58. SYNTHESIS OF BETA-LACTAMS FROM ACETIC-ACIDS AND IMINES PROMOTED BY VILSMEIER TYPE REAGENTS [J].
ARRIETA, A ;
LECEA, B ;
PALOMO, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (04) :845-850
[4]   TOTAL SYNTHESES OF PENICILLANIC ACID S,S-DIOXIDE AND 6-AMINOPENICILLANIC ACID USING (BENZYLOXY)NITROMETHANE [J].
BARRETT, AGM ;
SAKADARAT, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5110-5117
[5]   PREPARATION, MASS-SPECTRA, AND ACID-CATALYZED REARRANGEMENT OF ARYL-SUBSTITUTED AZETIDIN-2-ONES [J].
BIRD, PG ;
IRWIN, WJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (22) :2664-2670
[6]  
BOGDANOWICZSZWE.K, 1977, CHEM SCRIPTA, V51, P929
[7]  
BOGDANOWICZSZWED K, 1977, ROCZ CHEM, V51, P267
[8]   UBER N-[ALPHA-HALOGEN-ALKYL]-CARBONSAUREAMIDE .9. DIE GEWINNUNG VON BETA-LACTAMEN DURCH UMSETZUNG SCHIFFSCHER BASEN MIT CYANESSIGSAURE-HALOGENIDEN [J].
BOHME, H ;
EBEL, S ;
HARTKE, K .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1463-&
[9]  
BOSE AK, 1966, CHEM IND-LONDON, P903
[10]  
BOSE AK, 1972, TETRAHEDRON LETT, V40, P4091
123