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Synthesis and Reactivity of 1,4‐Oxazinoindole Derivatives
Author(s) -
Mayer Stanislas,
Mérour JeanYves,
Joseph Benoît,
Guillaumet Gérald
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200205)2002:10<1646::aid-ejoc1646>3.0.co;2-k
Subject(s) - chemistry , carboxylate , indole test , reactivity (psychology) , ethyl acrylate , electrophile , nitrogen atom , medicinal chemistry , michael reaction , acrylate , organic chemistry , stereochemistry , catalysis , group (periodic table) , medicine , alternative medicine , monomer , pathology , polymer
Application of the Hemetsberger reaction to ethyl 4‐benzyl‐7‐formyl‐2,3‐dihydro‐1,4‐benzoxazine‐2‐carboxylate ( 1 ) or acetate ( 2 ) afforded a mixture of ethyl 2,3,4,6‐tetrahydro‐[1,4]oxazino[2,3‐ f ]indole‐7‐carboxylate derivatives 3 or 4 and ethyl 2,3,4,9‐tetrahydro[1,4]oxazino[3,2‐ g ]indole‐8‐carboxylate derivatives 5 or 7 , with the “linear” derivatives predominant. Michael addition of tert ‐butyl acrylate to the indole nitrogen atom of 3 , 4 and subsequent electrophilic cyclisation gave access to tetracyclic compounds 24 , 25 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)