THE MECHANISM OF FORMATION OF 3H,9H-PYRANO[3,4-B]INDOL-3-ONES FROM 3-INDOLALKANOIC ACIDS

被引:0
作者
MEDIOSIMON, M [1 ]
ERFANIANABDOUST, H [1 ]
PINDUR, U [1 ]
机构
[1] UNIV MAINZ,FACHBEREICH CHEM & PHARM,INST PHARM,W-6500 MAINZ 1,GERMANY
来源
LIEBIGS ANNALEN DER CHEMIE | 1991年 / 06期
关键词
3H,9H-PYRANO[3,4-B]INDOLE DERIVATIVE; INDOLE DERIVATIVES;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The mechanism of the formation of 1-methyl-3H,9H-pyrano [3,4-b]indol-3-one (4) from the corresponding 3-indolacetic acid 1 is discussed. The suggested mechanism is substantiated by the isolation of a stable intermediate 2 and its transformations in the presence of acetic anhydride and/or Lewis acids.
引用
收藏
页码:601 / 602
页数:2
相关论文
共 13 条
[1]   A NEW PRECURSOR TO 3,4-DIDEHYDROPYRIDINE, AND ITS USE IN THE SYNTHESIS OF THE ANTITUMOUR ALKALOID ELLIPTICINE [J].
MAY, C ;
MOODY, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02) :247-250
[2]   DIELS-ALDER REACTIVITY OF PYRANO[3,4-B]INDOL-3-ONES, STABLE ANALOGS OF INDOLE-2,3-QUINODIMETHANES [J].
MOODY, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2505-2508
[3]   DIELS-ALDER REACTIVITY OF PYRANO[3,4-B]INDOL-3-ONES .2. STERIC AND ELECTRONIC EFFECTS IN THE ADDITION TO ALKYNES [J].
MOODY, CJ ;
SHAH, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1407-1415
[4]   DIELS-ALDER REACTIVITY OF PYRANO[3,4-B]INDOL-3-ONES .3. INTRAMOLECULAR DIELS-ALDER REACTIONS [J].
MOODY, CJ ;
SHAH, P ;
KNOWLES, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3249-3254
[5]  
PINDUR U, 1989, LIEBIGS ANN CHEM, P1275
[6]  
PINDUR U, 1989, LIEBIGS ANN CHEM, P227
[7]  
PINDUR U, 1988, LIEBIGS ANN CHEM, P803
[8]  
PINDUR U, 1988, CHIMIA, V42, P180
[9]   INDOLO-2,3-QUINODIMETHANES AND STABLE CYCLIC ANALOGS FOR REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESES OF [B]-ANELATED INDOLES [J].
PINDUR, U ;
ERFANIANABDOUST, H .
CHEMICAL REVIEWS, 1989, 89 (08) :1681-1689
[10]  
PINDUR U, 1990, LIEBIGS ANN CHEM, P771