UNPRECEDENTED REARRANGEMENT OF 5-BENZOYL SUBSTITUTED BICYCLIC ISOXAZOLIDINES TO DEHYDRO PYRROLIZIDIN-2-ONES AND INDOLIZIDIN-2-ONES

被引:4
作者
CORDERO, FM
BRANDI, A
DESARLO, F
VITI, G
机构
[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN U SCHIFF,I-50121 FLORENCE,ITALY
[2] UNIV FLORENCE,CNR,CTR COMPOSTI ETEROCICLICI,I-50121 FLORENCE,ITALY
[3] MENARINI IND FARMACEUT RINUITE SRL,I-50131 FLORENCE,ITALY
关键词
D O I
10.1039/c39940001047
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
5-Benzoyl substituted isoxazolidines 3, obtained by 1,3-dipolar cycloadditions of pyrroline N-oxide and tetrahydropyridine N-oxide to phenyl vinyl ketone, undergo a rearrangement to dehydro 3-phenyl-pyrrolizidin-2-one and 3-phenylindolizidin-2-one catalysed by Al2O3; the rearrangement products undergo a Michael addition to a second molecule of phenyl vinyl ketone.
引用
收藏
页码:1047 / 1048
页数:2
相关论文
共 26 条
[1]   REACTION OF AZOMETHINE OXIDES WITH ALLENES - NEW SYNTHESIS OF 3-PYRROLIDINONES [J].
AVERSA, MC ;
CUM, G ;
UCCELLA, N .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (03) :156-&
[2]  
BAMBERGER E, 1903, CHEM BER, V36, P1611
[3]   REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES [J].
BRANDI, A ;
DURUST, Y ;
CORDERO, FM ;
DESARLO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5666-5670
[4]   THE ISOXAZOLINE-5-SPIROCYCLOPROPANE ROUTE TO (+/-)-PUMILIOTOXIN-C [J].
BRANDI, A ;
CORDERO, FM ;
GOTI, A ;
GUARNA, A .
TETRAHEDRON LETTERS, 1992, 33 (44) :6697-6700
[5]  
BRANDI A, 1993, SYNLETT, P1
[6]  
Breuer E., 1989, NITRONES NITRONATES, P139
[7]  
Bruining WJ, 1922, RECL TRAV CHIM PAY-B, V41, P655
[8]  
CAMPS R, 1902, ARCH PHARM, V240, P423
[9]  
Confalone P. N., 1988, ORG REACTIONS, V36, P1
[10]   REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .10. REGIOSELECTIVE NITRONE CYCLOADDITIONS TO METHOXYCARBONYLMETHYLENECYCLOPROPANE - SYNTHESIS OF PRECURSORS OF (+/-)-LUPININE, (+/-)-EPILUPININE AND (+/-)-ELAEOKANINE-A [J].
CORDERO, FM ;
ANICHINI, B ;
GOTI, A ;
BRANDI, A .
TETRAHEDRON, 1993, 49 (43) :9867-9876