Facile and general synthesis of quaternary 3-aminooxindoles

被引:103
作者
Marsden, Stephen P. [1 ]
Watson, Emma L. [1 ]
Raw, Steven A. [2 ]
机构
[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England
[2] AstraZeneca Proc R&D, Macclesfield SK10 2NA, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1021/ol801028e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel approach to the valuable quaternary 3-aminooxindole skeleton is reported on the basis of intramolecular arylation of enolates of substituted amino acids. The reaction tolerates dialkyl- and arylalkylamines as well as a range of carbon substituents (primary and secondary alkyl, aryl). The cyclization of N-indolyl-substituted substrates is accompanied by direct C-H arylation of the indole, leading to indolo-fused benzodiazepines.
引用
收藏
页码:2905 / 2908
页数:4
相关论文
共 51 条
[1]   MARINE ALKALOIDS .12. CHARTELLINES, HALOGENATED BETA-LACTAM ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
ANTHONI, U ;
CHEVOLOT, L ;
LARSEN, C ;
NIELSEN, PH ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4709-4712
[2]   Development of an N-heterocyclic carbene ligand based on concept of chiral mimetic [J].
Arao, T ;
Kondo, K ;
Aoyama, T .
TETRAHEDRON LETTERS, 2006, 47 (09) :1417-1420
[3]   Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular α-arylation [J].
Arao, Takafumi ;
Kondo, Kazuhiro ;
Aoyama, Toyohiko .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (12) :1743-1747
[4]   X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .28. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES - BACKGROUND AND REACTION OF AMINES WITH BIFUNCTIONAL KETONES [J].
ARDILL, H ;
DORRITY, MJR ;
GRIGG, R ;
LEONLING, MS ;
MALONE, JF ;
SRIDHARAN, V ;
THIANPATANAGUL, S .
TETRAHEDRON, 1990, 46 (18) :6433-6448
[5]   New Heck coupling strategies for the synthesis of paullone and dimethyl paullone [J].
Avila-Zarraga, Jose Gustavo ;
Lujan-Montelongo, Armando ;
Covarrubias-Zuniga, Adrian ;
Romero-Ortega, Moises .
TETRAHEDRON LETTERS, 2006, 47 (45) :7987-7989
[6]   5-Amidinoindoles as dual inhibitors of coagulation factors IXa and Xa [J].
Batt, DG ;
Qiao, JX ;
Modi, DP ;
Houghton, GC ;
Pierson, DA ;
Rossi, KA ;
Luettgen, JM ;
Knabb, RM ;
Jadhav, PK ;
Wexler, RR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (21) :5269-5273
[7]   Practical and efficient palladium-promoted synthesis of indole systems containing medium- and large-ring-fused heterocycles [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Paladino, Giuseppe ;
Rossi, Elisabetta .
SYNTHESIS-STUTTGART, 2006, 14 (14) :2404-2412
[8]   TANDEM RADICAL TRANSLOCATION AND HOMOLYTIC AROMATIC-SUBSTITUTION - A CONVENIENT AND EFFICIENT ROUTE TO OXINDOLES [J].
BECKWITH, ALJ ;
STOREY, JMD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (09) :977-978
[9]   Approach to 3-aminoindolin-2-ones via oxime ether functionalized carbamoylcyclohexadienes [J].
Bella, AF ;
Slawin, AMZ ;
Walton, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :5926-5933
[10]   Addition of chiral enolates to N-alkyl-3-acylpyridinium salts.: Total synthesis of (+)-16-epivinoxine and (-)-vinoxine [J].
Bennasar, ML ;
Zulaica, E ;
Alonso, Y ;
Vidal, B ;
Vázquez, JT ;
Bosch, J .
TETRAHEDRON-ASYMMETRY, 2002, 13 (01) :95-106