IBX-promoted domino reaction of α-hydroxy amides: a facile one-pot synthesis of isatins

Abstract

A novel and temperature-controlled oxidation of α-hydroxy amides in the presence of IBX is described.

The Mechanistic Perspective of IV Iodoxolones

“…In 2016, Wang et al. manipulated this handle during glycolic acid N‐ methylanilide 367 (Scheme 61) oxidation, to chemoselectively trap N‐ methyl‐ N‐ phenyl‐2‐oxoacetamide 368 or form N‐ methylistatin 370 [107] …”

“…In 2016, Wang et al manipulated this handle during glycolic acid N-methylanilide 367 (Scheme 61) oxidation, to chemoselectively trap N-methyl-N-phenyl-2-oxoacetamide 368 or form N-methylistatin 370. [107] Wang et al proposed a reaction mechanism initiated from dehydrogenation of the α-hydroxy amide terminal hydroxyl group in the presence of IBX 3, forming the aldehyde terminus of α-formyl amide 368. As denoted by the insets of Scheme 61, the reaction does not preceed through cyclisation at room temperature, which allows product 368 to be isolated in excellent yield.…”

A Mild and Eco-friendly, One-pot Synthesis of 2-hydroxy-Narylacetamides from 2-chloro-N-arylacetamides

“…3Aryl-2-hydroxy amides were synthesized by regioselective ring opening of 2,3-epoxy amides using active manganese [22]. The use of these synthetic intermediates was demonstrated in an e cient and eco-friendly one-pot metal-free synthesis of isatins by IBX [23] or H 2 O 2 as the oxidant [24]. Indole fused 2-hydroxy amides were obtained by different strategies such as Friedel-Crafts hydroxyalkylation of indole with α-keto amides in the presence of K 3 PO 4 and n Bu 4 NBr in aqueous medium [25], palladium mediated coupling of ortho-halo substituted anilides with α-keto amides in toluene [26] as well as by nickel in DME and THF [27], TFA or scandium promoted intramolecular Friedel-Crafts reaction [28,29] and zinc-catalyzed chemoselective addition [30].…”