Electrophilic substitution of indoles catalyzed by triphenyl phosphonium perchlorate:: Synthesis of 3-acetyl indoles and bis-indolylmethane derivatives

被引:73
作者
Nagarajan, R [1 ]
Perumal, PT [1 ]
机构
[1] Cent Leather Res Inst, Div Organ Chem, Chennai 600020, Tamil Nadu, India
关键词
D O I
10.1081/SCC-120001515
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triphenyl phosphonium perchlorate (TPP) is found to catalyze the acetylation of indoles with acetic anhydride to give 3-acetyl indoles. Similarly bis-indolylmethane derivatives were prepared by the electrophilic substitution reaction of indole with substituted benzaldehydes.
引用
收藏
页码:105 / 109
页数:5
相关论文
共 13 条
[1]  
DOROFEENKO GN, 1960, ZH VKHO DI MENDELEEV, V5, P354
[2]   ALKALOIDS OF OCHROSIA POWERI BAILEY .2. 2-ACYLINDOLE STEM-BARK BASES [J].
DOUGLAS, B ;
MOORE, BP ;
WEISBACH, JA ;
KIRKPATRICK, JL .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (02) :246-&
[3]  
FOLDEAK S, 1965, ACTA PHYS CHEM, V11, P115
[4]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075
[5]   SYNTHESIS AND DIELS-ALDER REACTIONS OF 1,3-DIMETHYL-4-(PHENYLSULFONYL)-4H-FURO[3,4-B]INDOLE - A NEW ANNULATION STRATEGY FOR THE CONSTRUCTION OF ELLIPTICINE AND ISOELLIPTICINE [J].
GRIBBLE, GW ;
SAULNIER, MG ;
SIBI, MP ;
OBAZANUTAITIS, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4518-4523
[6]   SYNTHESES AND DIELS-ALDER CYCLOADDITION REACTIONS OF 4H-FURO[3,4-B]INDOLES - A REGIOSPECIFIC DIELS-ALDER SYNTHESIS OF ELLIPTICINE [J].
GRIBBLE, GW ;
KEAVY, DJ ;
DAVIS, DA ;
SAULNIER, MG ;
PELCMAN, B ;
BARDEN, TC ;
SIBI, MP ;
OLSON, ER ;
BELBRUNO, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5878-5891
[7]   SYNTHESIS AND CYCLOADDITION OF 2,4-DIHYDROPYRROLO[3,4-B]INDOLES [J].
JEEVANANDAM, A ;
SRINIVASAN, PC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20) :2663-2665
[8]  
KOST AN, 1964, J GEN CHEM USSR, V34, P3025
[9]  
NAGARAJAN R, 2001, IN PRESS TETRAHEDRON
[10]   A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride [J].
Okauchi, T ;
Itonaga, M ;
Minami, T ;
Owa, T ;
Kitoh, K ;
Yoshino, H .
ORGANIC LETTERS, 2000, 2 (10) :1485-1487