Silver- versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone
A Arcadi1, M Chiarini2, L Del Vecchio3
1Dipartimento di Scienze Fisiche e Chimiche, Università di L'Aquila, Via Vetoio-67010 Coppito (AQ), Italy. antonio.arcadi@univaq.it.
Abstract:
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.
Related Concept Videos
Oxidations of Aldehydes and Ketones to Carboxylic Acids
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkynes to Carboxylic Acids: Oxidative Cleavage
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)