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 | Zendy

Yang Weibo | Zendy; Wang Tao | Zendy; Yu Yang | Zendy; Shi Shuai | Zendy; Zhang Tuo | Zendy; Hashmi A. Stephen K. | Zendy

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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.

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