Diels-Alder and Michael addition reactions of indoles with masked o-benzoquinones: Synthesis of highly functionalized hydrocarbazoles and 3-arylindoles

Chemical Communications

Volumn , Issue 15, 1999, Pages 1441-1442

  Hsieh, Ming Fang ^a   Rao, Polisetti Dharma ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; CARBAZOLE DERIVATIVE; GUAIACOL; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0033533164     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904366g     Document Type: Article

References (29)

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28. Procedure for Diels-Alder or Michael addition reactions of indoles 3 with la-c. To a solution of 2 (1.0 mmol) in MeOH (10 ml) at 0 CC was added DAIB (1.0 mmol). After 10 min of stirring, an indole derivative 3 (5-20 mmol) was added at that temperature and the flask was rapidly warmed up to room temperature or to that of reflux by either removing the ice bath or transferring the reaction vessel to a preheated ( 100 C) oil bath. The reaction mixture was stirred at either temperature for 1 h. Then MeOH was removed and the residue obtained was purified by flash chromatography on silica gel using 20% of ethyl acetate in hexanes as eluent to obtain Diels-Alder adducts or aromatized Michael adducts.
29. int = 0.0347). Final R indices [I > 2σ(I)] R1 = 0.0349, wR2 = 0.0893. CCDC 182/1310. See http://www.rsc.org/suppdata/cc/1999/1441/ for crystallographic data in .cif format.