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Nitrones as Trapping Reagents of α,β‐Unsaturated Carbene Intermediates – [1,2]Oxazino[5,4‐ b ]indoles by a Platinum‐ Catalyzed Intermolecular [3+3] Cycloaddition
Author(s) -
Yang Weibo,
Wang Tao,
Yu Yang,
Shi Shuai,
Zhang Tuo,
Hashmi A. Stephen K.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300338
Subject(s) - chemistry , cycloaddition , carbene , intramolecular force , intermolecular force , trifluoromethyl , catalysis , medicinal chemistry , platinum , nitro , intramolecular reaction , reagent , photochemistry , organic chemistry , molecule , alkyl
Some readily available Boc‐protected 2‐(3‐methoxy‐1‐propynyl)anilines and nitrones in platinum‐catalyzed reactions deliver [1,2]oxazino[5,4‐ b ]indoles. Twelve examples with yields of 41–95% are reported. Different substituents like nitro, trifluoromethyl, fluoro, bromo, and ester groups are tolerated. With regard to the mechanism, this reaction probably combines an initial intramolecular cyclization/elimination to vinylcarbenoid species and a subsequent stepwise intermolecular [3+3] cycloaddition with the nitrones.