Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acid-mediated cyclizations: Generality, scope, and mechanism
The discovery and development of the o-iodoxybenzoic acid (IBX) reaction with certain unsaturated N-aryl amides (anilides) to form heterocycles are described. The application of the method to the synthesis of δ-lactams, cyclic urethanes, hydroxy amines, and amino sugars among other important building blocks and intermediates is detailed. In addition to the generality and scope of this cyclization reaction, this article describes a number of mechanistic investigations suggesting a single electron transfer from the anilide functionality to IBX and implicating a radical-based mechanism for the reaction.
Nicolaou,Baran,Zhong,Barluenga,Hunt,Kranich,Vega
p. 2233 - 2244
(2007/10/03)
Synthesis of 3,6-dihydro-1(2H)-pyridinyl derivatives with hyperglycemic activity
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Yeung,Knaus
p. 181 - 185
(2007/10/02)
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