Reactions involving aryl methyl ketone and molecular iodine: a powerful tool in the one-pot synthesis of heterocycles

Abstract

The preparation of heterocyclic compounds has attracted great attention in organic chemistry because of their extensive presence in bioactive molecules, material sciences, and natural products. Accordingly, the straightforward design and...

TEMPO mediated oxidative annulation of aryl methyl ketones with amines/ammonium acetate for imidazole synthesis

“…For example, 1 H -imidazole 3a underwent 5-bromination and subsequent Sonogashira coupling to give a more functionalized compound 6 in a high yield (Scheme 2(2)). 1–12,14–21 The above results demonstrated the practicality of this protocol.…”

“…13 Aryl methyl ketones are the ideal synthons in most reactions, and can be readily prepared by the classical Friedel–Crafts acylation and Wacker-type reactions. 14 Undoubtedly, compared with the known strategies, direct oxidative annulation of aryl methyl ketones with amines is an atom- and step-economical approach for the construction of imidazole skeletons. In 2012, Wang's group 12 and Wang and Ji's group 15 realized this strategy in the presence of I 2 /TBHP and CuI/BF 3 ·Et 2 O, respectively, for the synthesis of 1 H -imidazoles.…”

Traveling across Life Sciences with Acetophenone—A Simple Ketone That Has Special Multipurpose Missions

“…Both plant metabolism and chemical synthesis provide us with the molecular acetophenone family, an interesting group of alkyl-phenylketones that have an aromatic homomonocyclic framework. Owing to its chemical nature and reactivity, acetophenone, the parent of this family, is one of the most useful precursors in heterocyclic synthesis [ 76 , 77 , 78 ] and the ideal synthon for multicomponent reactions based on simple aldol condensations or the α-functionalization strategy [ 79 ], allowing the preparation of various natural product analogs and pharmaceuticals with important biological properties.…”

Aryl Methyl Ketones: Versatile Synthons in the Synthesis of Heterocyclic Compounds

“…and reducing possible toxicity concerns. The increasing presence of various aromatic heterocycles in drugs is no doubt related to advances in synthetic methodology such as metal-catalyzed cross-couplings, 1a hetero-couplings, 1b and metal-free conditions, 1c , d enabling rapid access to a wide variety of functionalized heterocyclic scaffolds.…”

“…Iodine, in combination with AMKs, can substitute for several transition metals used in previously reported transformations while also maintaining an excellent atom economy. 1e , f , j This aspect, along with the commercial abundance and cost-effective nature of AMKs, provides an incentive to the research community to discover and further develop such processes for use in drug discovery. Despite the vast literature that has evolved on this topic, there has yet to be a succinct review of the important developments in this area.…”