INDOLE 3-ACETIC ACIDS AND HETERO ANALOGS BY ONE-POT SYNTHESIS INCLUDING HECK CYCLIZATION

被引:41
作者
WENSBO, D
ANNBY, U
GRONOWITZ, S
机构
[1] CTR CHEM,DEPT ORGAN CHEM 1,S-22100 LUND,SWEDEN
[2] SYNTHELEC AB,IDEON,S-22370 LUND,SWEDEN
关键词
D O I
10.1016/0040-4020(95)00601-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bz-substituted indole-3-acetic acid ethyl esters (14e-g) and heteroanalogues, i.e. thienopyrroles (14a, c) and selenolopyrrole (14d), were prepared starting from N-BOC protected o-iodo aryl amines. Allylation with ethyl 4-bromocrotonate, followed by palladium-catalysed ring closure in a one pot reaction, yielded N-BOC protected indoles (13e-g), thienopyrroles (13a-c), and selenolopyrrole (13d). The BOC group was readily removed thermally after adsorption on silica. Oxothienopyrroles (11a-c) were similarly prepared.
引用
收藏
页码:10323 / 10342
页数:20
相关论文
共 53 条
[1]   SYNTHESIS OF 3,4-BRIDGED INDOLES BY PHOTOCYCLIZATION REACTIONS .2. PHOTOCYCLIZATION OF HALOGENOACETYL TRYPTOPHOL DERIVATIVES AND ALPHA-CHLORO INDOL-3-YLALKANOATE ESTERS [J].
BECK, AL ;
MASCAL, M ;
MOODY, CJ ;
COATES, WJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (07) :813-821
[2]   AMIDOMERCURATION-CYCLIZATION OF N-TERT-BUTOXYCARBONYL-2-ALLYLANILINE DERIVATIVES [J].
BERGER, J ;
KERLY, DL .
HETEROCYCLES, 1993, 36 (09) :2051-2058
[3]   THIOPHENE AS A STRUCTURAL ELEMENT OF PHYSIOLOGICALLY ACTIVE COMPOUNDS .1. SYNTHESIS OF DERIVATIVES OF 4-THIENO[2,3-B]-PYRROLEACETIC ACID [J].
BINDER, D ;
NOE, CR ;
HABISON, G ;
CHOCHOLOUS, J .
ARCHIV DER PHARMAZIE, 1979, 312 (02) :169-174
[4]   SYNTHESIS OF ARCYRIARUBIN B AND RELATED BISINDOLYLMALEIMIDES [J].
BRENNER, M ;
REXHAUSEN, H ;
STEFFAN, B ;
STEGLICH, W .
TETRAHEDRON, 1988, 44 (10) :2887-2892
[5]   HETEROCYCLIC AMINES .V. ELECTROPHILIC SUBSTITUTION IN SOME CARBAMATE DERIVATIVES OF 3-AMINOTHIOPHENE [J].
BRUNETT, EW ;
MCCARTHY, WC .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1968, 57 (11) :2003-&
[6]   AN EFFICIENT, PALLADIUM-CATALYZED ROUTE TO PROTECTED ALLYLIC AMINES [J].
CONNELL, RD ;
REIN, T ;
AKERMARK, B ;
HELQUIST, P .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3845-3849
[7]   AN ANNULATION METHOD FOR THE SYNTHESIS OF HIGHLY SUBSTITUTED POLYCYCLIC AROMATIC AND HETEROAROMATIC-COMPOUNDS [J].
DANHEISER, RL ;
BRISBOIS, RG ;
KOWALCZYK, JJ ;
MILLER, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3093-3100
[8]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[9]   POTENTIAL ANTICANCER AGENTS .74. ALKYLATING AGENTS DERIVED FROM INDOLE .3. SYNTHESIS OF SOME INDOLEALKANOIC ACID NITROGEN MUSTARDS [J].
DEGRAW, J ;
GOODMAN, L .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) :1728-&
[10]   FIRST EXAMPLE OF A 1-AMINOQUINAZOLINE-2,4-DIONE [J].
DEMERS, JP .
TETRAHEDRON LETTERS, 1994, 35 (35) :6425-6426