Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a ‘green’ analog of Koser’s reagent

Justik, Michael W.

doi:10.1016/j.tetlet.2007.02.129

Cited by 23 publications

(7 citation statements)

References 27 publications

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“…Several other hypervalent iodine heterocycles incorporating phosphorus, ,, sulfur, ,,,− and boron atoms in the ring have been synthesized and characterized by X-ray crystallography. The reactivity of these heterocyclic iodine compounds has been less inverstigated.…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…In 2007, the ring contraction of 1-benzosuberone 74 to methyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate (76) was reported in 88% yield using 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide (HMBI, 75), although a similar ring contraction product with 1-indanone or 1-tetralone was not observed. 32 In addition, the flavanone 77 affords methyl 2,3-dihydro-2-phenyl-3-benzofurancarboxylate (78) in 68% yield under similar reaction conditions (Scheme 26). 32…”

Section: Ring Contractionsmentioning

confidence: 93%

Oxidative Rearrangements with Hypervalent Iodine Reagents

Singh

Wirth

2013

Synthesis

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Hypervalent iodine chemistry is used as an important tool in synthetic and natural product chemistry. A number of hypervalent iodine reagents can be used to generate the functionalizations on various scaffolds by several chemical approaches including oxidation reactions, oxidative cyclization reactions, and rearrangements. Recently, these reagents have been employed to develop a variety of oxidative rearrangements. In this review article, various aspects of recently developed oxidative rearrangements using iodine(III) and iodine(V) reagents are described. 1 Introduction 2 Oxidative Rearrangements 2.1 1,2-Aryl Group Migrations 2.2 Hofmann Rearrangements 2.2.1 Hofmann Rearrangements without Cyclizations 2.2.2 Hofmann Rearrangements with Cyclizations 2.3 Ring Contractions 2.4 Ring Expansions

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“…As such, alternative ring expansions were considered. One such alternative that was considered utilizes a hypervalent iodide to facilitate a 1,2-shift …”

Section: Process Developmentmentioning

confidence: 99%

Development of a Process Route to the FAK/ALK Dual Inhibitor TEV-37440

Allwein

Mowrey

Petrillo

et al. 2017

Org. Process Res. Dev.

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The development of a scalable route to TEV-37440, a dual inhibitor of focal adhesion kinase (FAK) and anaplastic lymphoma kinase (ALK), is presented. The medicinal chemistry route used to support this target through nomination is reviewed, along with the early process chemistry route to support IND (inversigational new drug) enabling activities within CMC (Chemistry, Manufacturing, and Controls). The identification and development of an improved route that was performed in the pilot plant to supply early phase clinical supplies are discussed. Details surrounding the use of a novel ring expansion, a selective nitration through a para-blocking group strategy, a single-pot amination–hydrogenation, a diastereomeric salt resolution, a through-process step to avoid a hazardous intermediate, and a practical formation of a trihydrochloride dihydrate salt are disclosed.

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Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a ‘green’ analog of Koser’s reagent

Cited by 23 publications

References 27 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Oxidative Rearrangements with Hypervalent Iodine Reagents

Development of a Process Route to the FAK/ALK Dual Inhibitor TEV-37440

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