1,3-dipolar cycloaddition of 3-arylidenechromanone-1-thiochromanone and -flavanone: Regio- and stereoselective formation of spiroheterocycles

被引:20
作者
Fisera, L
Jaroskova, L
Levai, A
Jedlovska, E
Toth, G
Polakova, M
机构
[1] LAJOS KOSSUTH UNIV, DEPT ORGAN CHEM, H-4010 DEBRECEN, HUNGARY
[2] TECH UNIV BUDAPEST, INST GEN & ANALYT CHEM, H-1111 BUDAPEST, HUNGARY
关键词
D O I
10.3987/COM-97-7860
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cycloaddition of nitrile oxides, nitrones, and nitrile imines to 3-arylidenechromanone (1), -flavanone (5), -1-thiochromanone (2) and -1-tetralone (3) proceeds regio-and stereoselectively under the formation of spiro-substituted isoxazole and pyrazole derivatives.
引用
收藏
页码:1651 / 1655
页数:5
相关论文
共 10 条
[1]   1,3-DIPOLAR CYCLOADDITION OF NITRONES AND NITRILE OXIDES TO 5,5-DIMETHYL-3-METHYLENEPYRROLIDINE-2-THIONE [J].
FISERA, L ;
JAROSKOVA, L ;
MATEJKOVA, I ;
HEIMGARTNER, H .
HETEROCYCLES, 1995, 40 (01) :271-278
[2]   1,3-DIPOLAR CYCLOADDITION ON HETEROCYCLES .31. CYCLOADDITIONS OF NITRILE OXIDES AND NITRONES TO 4,4-METHYLENE-1-METHYLPIPERIDINE - STUDIES IN REGIOSELECTIVITY AND STEREOSELECTIVITY [J].
FISERA, L ;
SAUTER, F ;
FROHLICH, J ;
FENG, Y ;
ERTL, P ;
MEREITER, K .
MONATSHEFTE FUR CHEMIE, 1994, 125 (05) :553-563
[3]  
FISERA L, 1992, ACS MONOGR SER, P158
[5]   PUREALIDIN-B AND PUREALIDIN-C, NEW BROMOTYROSINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE PSAMMAPLYSILLA-PUREA [J].
KOBAYASHI, J ;
TSUDA, M ;
AGEMI, K ;
SHIGEMORI, H ;
ISHIBASHI, M ;
SASAKI, T ;
MIKAMI, Y .
TETRAHEDRON, 1991, 47 (33) :6617-6622
[6]   ARAPLYSILLIN-I AND ARAPLYSILLIN-II - BIOLOGICALLY-ACTIVE DIBROMOTYROSINE DERIVATIVES FROM THE SPONGE PSAMMAPLYSILLA-ARABICA [J].
LONGEON, A ;
GUYOT, M ;
VACELET, J .
EXPERIENTIA, 1990, 46 (05) :548-550
[7]   REGIO-DIPOLAR AND STEREOSELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF C,N-DIARYLNITRONES TO 3,3-METHYLENE-5,5-DIMETHYL-2-PYRROLIDINONE [J].
ORAVEC, P ;
FISERA, L ;
GOLJER, I ;
ERTL, P .
MONATSHEFTE FUR CHEMIE, 1991, 122 (11) :977-985
[8]   1,3-DIPOLAR CYCLOADDITION ON HETEROCYCLES .25. REGIOSELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO 3,3-METHYLENE-5,5-DIMETHYL-2-PYRROLIDINONE [J].
ORAVEC, P ;
FISERA, L ;
ERTL, P ;
VEGH, D .
MONATSHEFTE FUR CHEMIE, 1991, 122 (10) :821-828
[9]   SYNTHESIS AND STEREOCHEMISTRY OF SPIROPYRAZOLINES [J].
TOTH, G ;
SZOLLOSY, A ;
LEVAI, A ;
KOTOVYCH, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (12) :1895-1898
[10]   STEREOCHEMISTRY OF 3-ARYLIDENEFLAVANONES AND THEIR THIO ANALOGS BY THE USE OF 3J(CH) COUPLINGS [J].
TOTH, G ;
SZOLLOSY, A ;
LEVAI, A ;
OSZBACH, G ;
DIETRICH, W ;
KUHNE, H .
MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (08) :801-804