Diels-Alder trapping of 3-methylenequinolin-2,4-dione: a facile synthesis of pyranoquinolinones and spiroquinolinediones

被引:19
作者
Nair, V [1 ]
Treesa, PM
Jayan, CN
Rath, NP
Vairamani, M
Prabhakar, S
机构
[1] CSIR, Reg Res Lab, Div Organ Chem, Trivandrum 695019, Kerala, India
[2] Univ Missouri, Dept Chem, St Louis, MO 63121 USA
[3] Indian Inst Chem Technol, Div Analyt Chem, Hyderabad, Andhra Pradesh, India
关键词
cycloaddition; dienes; enol ethers; quinolines;
D O I
10.1016/S0040-4020(01)00704-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Methylenequinolin-2,4-dione generated in situ by Knoevenagel condensation of 4-hydroxyquinoline with formaldehyde is trapped by Diels-Alder cycloaddition to provide spiroquinolinediones and pyranoquinolinones. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7711 / 7717
页数:7
相关论文
共 18 条
[1]   GENERAL AND PRACTICABLE SYNTHESIS OF POLYCYCLIC HETEROAROMATIC-COMPOUNDS .1. USE OF A PUTATIVE QUINOLONE-QUINONE-METHIDE IN THE SYNTHESIS OF POLYCYCLIC HETEROAROMATIC-COMPOUNDS [J].
ASHERSON, JL ;
YOUNG, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02) :512-521
[2]   DIELS-ALDER VERSUS HETERODIENE IN THE REACTION BETWEEN 4-ARYLIDENE-5-PYRAZOLONES AND 2,3-DIMETHYLBUTADIENE - THE EFFECT OF ACID CATALYSIS [J].
BRUGNOLOTTI, M ;
CODA, AC ;
DESIMONI, G ;
FAITA, G ;
INVERNIZZI, AG ;
RIGHETTI, PP ;
TACCONI, G .
TETRAHEDRON, 1988, 44 (16) :5229-5242
[3]  
CHAUNCEY MA, 1990, SYNTHESIS-STUTTGART, P1005
[4]   GENERATION OF HETEROCYCLIC QUINONE METHIDES FROM ORTHO-HYDROXY METHYL-DERIVATIVES AND A STUDY OF THEIR CYCLO-ADDITION REACTIONS [J].
CHAUNCEY, MA ;
GRUNDON, MF ;
RUTHERFORD, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (08) :527-529
[5]   CHEMICAL AND BIOACTIVE CONSTITUENTS FROM ZANTHOXYLUM SIMULANS [J].
CHEN, IS ;
WU, SJ ;
TSAI, IL ;
WU, TS ;
PEZZUTO, JM ;
LU, MC ;
CHAI, H ;
SUH, N ;
TENG, CM .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1206-1211
[6]   HETERODIENE SYNTHESES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
DESIMONI, G ;
TACCONI, G .
CHEMICAL REVIEWS, 1975, 75 (06) :651-692
[7]  
EISENSTEIN O, 1977, TETRAHEDRON, V33, P523
[8]   A DIELS-ALDER ADDUCT OF N-METHYLFLINDERSINE AND A QUINOLONE QUINONE METHIDE [J].
GRUNDON, MF ;
RAMACHANDRAN, VN ;
SLOAN, BM .
TETRAHEDRON LETTERS, 1981, 22 (32) :3105-3108
[9]   SYNTHESES OF FLUORESCENT DYES .9. NEW 4-HYDROXYCOUMARINS, 4-HYDROXY-2-QUINOLONES, 2H,5H-PYRANO[3,2-C]BENZOPYRAN-2,5-DIONES AND 2H,5H-PYRANO[3,2-C]QUINOLINE-2,5-DIONES [J].
KNIERZINGER, A ;
WOLFBEIS, OS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (02) :225-229
[10]   Total syntheses of pyranoquinoline alkaloids:: Simulenoline, huajiaosimuline, and (±)-7-demethoxyzanthodioline [J].
McLaughlin, MJ ;
Hsung, RP .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :1049-1053