Silver- versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone

Unprecedented domino oxidative cyclization reactions of unprotected 2-alkynylanilines to give functionalized 4H-benzo[d][1,3]oxazin-4-one or benzisoxazole derivatives in moderate to good yields are achieved by silver vs. gold selective catalysis. The search for the optimal reaction conditions reveal...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (7), p.1458-1461
Main Authors: Arcadi, A, Chiarini, M, Del Vecchio, L, Marinelli, F, Michelet, V
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Catalysis
Cyclization
Gold - chemistry
Oxidation-Reduction
Silver - chemistry
Sulfuric Acids - chemistry
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Summary:Unprecedented domino oxidative cyclization reactions of unprotected 2-alkynylanilines to give functionalized 4H-benzo[d][1,3]oxazin-4-one or benzisoxazole derivatives in moderate to good yields are achieved by silver vs. gold selective catalysis. The search for the optimal reaction conditions revealed the divergent catalytic activity of NaAuCl4·H2O and AgNO3.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08543h