Generation of N-(tert-Butoxycarbonyl)indole-2,3-quinodimethane and Its [4+2]-Type Cycloaddition

The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K2CO3 or Pd2(dba)3 in refluxing toluene. The resulting N-(tert-butoxycar...

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Veröffentlicht in:	Journal of organic chemistry 2009-08, Vol.74 (16), p.6402-6405
Hauptverfasser:	Inagaki, Fuyuhiko, Mizutani, Masaya, Kuroda, Norikazu, Mukai, Chisato
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes - chemistry Alkynes - chemistry Aniline Compounds - chemistry Carbonates - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles - chemical synthesis Indoles - chemistry Noncondensed benzenic compounds Organic chemistry Organometallic Compounds - chemistry Potassium - chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K2CO3 or Pd2(dba)3 in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the corresponding tetrahydro- and dihydrocarbazole derivatives.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo901325d