Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Yoshimura, Atsushi; Jarvi, Melissa E.; Shea, Michael T.; Makitalo, Cody L.; Rohde, Gregory T.; Yusubov, Mekhman S.; Saitô, Akio; Zhdankin, Viktor V.

doi:10.1002/ejoc.201901258

Cited by 19 publications

(13 citation statements)

References 63 publications

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“…37 In 2019, Yoshimura exploited the regioselective cycloaddition of aldoximes with enaminones by employing Koser's reagent [PhI(OH)OTs] to construct 3,4-disubstituted isoxazoles, in which aldoximes could be oxidized to the nitrile oxide by PhI(OH)OTs (Scheme 35). 38 In 2019, Fu (Scheme 36) 39 and Zhou (Scheme 37) 40 independently developed the reaction of enaminones and elemental sulfur (as the sulfur source) to synthesize 2-amino-5-acylthiazoles and 5-acyl-1,2,3-thiadiazoles in one pot. Additionally, cyanamide (NH 2 CN) and tosylhydrazine (TsNHNH 2 ) were used as the nitrogen sources, respectively.…”

Section: Scheme 33 Iodine-promoted Regioselective Construction Of 15mentioning

confidence: 99%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

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Enaminones are gaining increasing interest because of their unique properties and their importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, and allow further elaboration via a range of facile chemical transformations. Over the past five years, there have been an increasing number of reports describing the synthetic applications of N,N-dimethyl enaminones. This review provides a comprehensive overview on the synthetic applications of N,N-dimethyl enaminones that have been reported since 2016.1 Introduction2 Direct C(sp2)–H α-Functionalization2.1 Synthesis of α-Sulfenylated N,N-Dimethyl Enaminones2.2 Synthesis of α-Thiocyanated N,N-Dimethyl Enaminones2.3 Synthesis of α-Acyloxylated N,N-Dimethyl Enaminones3 Functionalization Reactions via C=C Double Bond Cleavage3.1 Synthesis of Functionalized Methyl Ketones3.2 Synthesis of α-Ketoamides, α-Ketoesters and 1,2-Diketones3.3 Synthesis of N-Sulfonyl Amidines4 Construction of All-Carbon Aromatic Scaffolds4.1 Synthesis of Benzaldehydes4.2 Synthesis of the Naphthalenes5 Construction of Heterocyclic Scaffolds5.1 Synthesis of Five-Membered Heterocycles5.2 Synthesis of Six-Membered Heterocycles5.3 Synthesis of Quinolines 5.4 Synthesis of Functionalized Chromones5.5 Synthesis of Other Fused Polycyclic Heterocycles6 Conclusions and Perspectives

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Section: Scheme 33 Iodine-promoted Regioselective Construction Of 15mentioning

confidence: 99%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

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“…Isoxazoles belong to an important class of heteroaromatic compounds with many practical applications. 52 Hypervalent iodine reagents such as (diacetoxyiodo)benzene, 116,122,[142][143][144][145][146][147] [bis(trifluoroacetoxy)iodo]benzene, 136,[148][149][150][151] iodosylbenzene, 134,135 [hydroxy(tosyloxy)iodo]benzene, 152,153 and in situ generated iodine(III) species 138,154 have been commonly used for isoxazole ring construction.…”

Section: Synthesis Of Isoxazolesmentioning

confidence: 99%

“…Very recently, our group reported the regioselective cycloaddition reaction of aldoximes with enaminones. 153 The reaction of aldoximes 98 with enaminones 99 and [hydroxy(tosyloxy)iodo]benzene afforded the 3,4-disubstituted isoxazoles 100 (Scheme 26). This reaction involves the regioselective cycloaddition of enaminones with the generated nitrile oxide followed by elimination of dialkylamine to produce 3,4-disubstituted isoxazole products 100.…”

Section: Synthesis Of Isoxazolesmentioning

confidence: 99%

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

et al. 2020

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Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summarize the hypervalent-iodine-mediated preparation of oxazolines, oxazoles, isoxazolines, and isoxazoles starting from various substrates.1 Introduction2 Synthesis of Oxazolines3 Synthesis of Oxazoles4 Synthesis of Isoxazolines5 Synthesis of Isoxazoles6 Conclusion

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“…The chemistry of β‐dimethylaminovinyl ketones – commonly known as β‐enaminones – has been widely explored for nearly 60 years, and the vast majority of heterocycles have been synthesized using them as starting materials. [ 1 ] Among these, azoles – such as triazolo/tetrazolo[1,5‐ a ]pyrimidines, [ 2–5 ] 1,2,3‐triazoles, [ 6 ] benzimidazoles, [ 7 ] pyrazoles, [ 8–10 ] pyrroles, [ 11,12 ] isoxazoles, [ 13,14 ] thiazoles [ 15 ] – and furans, [ 16 ] and other six‐membered heterocycles – such as quinolines, [ 17–19 ] pyridines, [ 20,21 ] chromones, [ 22 ] and oxathiines [ 23 ] – have been prepared by using β‐enaminones through formal [3+2] or [3+3] cyclocondensation or cycloaddition reactions, with a variety of reagents ( N,N‐ or N,O ‐dinucleophiles, NCN ‐dinucleophiles, etc. ), catalysts, and specific reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

The Wonderful World of β‐Enamino Diketones Chemistry

et al. 2020

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The simple preparation and functionalization of oxa/aza heterocycles requires new and efficient starting materials to be discovered so that regioselective methodologies with a wide range of applications in organic synthesis can be developed. With this in mind, β‐enamino diketones have emerged as a suitable building block for preparing the most diverse (poly)heterocyclic systems, through cyclocondensation or cycloaddition reactions. This review compiles all the reactions that have been conducted using these starting materials, ever since they were first disclosed in 1980.

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Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Cited by 19 publications

References 63 publications

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

The Wonderful World of β‐Enamino Diketones Chemistry

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