A New Method for the Synthesis of Iminoquinones via DMP-Mediated Oxidative Reaction

Ma, Hengchang; Wu, Shang; Sun, Qizhen; Li, Hongyan; Chen, Yannan; Zhao, Wenqing; Ma, Bihui; Guo, Qing; Lei, Ziqiang; Yan, Jun

doi:10.1055/s-0030-1258202

Cited by 10 publications

(3 citation statements)

References 17 publications

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“…DMP has been used in the synthesis of polycyclic compounds and heterocycles. − Nicolaou and co-workers have reported the DMP-mediated cyclization of anilides affording the natural product-like heterocyclic compounds. For example, the reaction of anilide 576 with DMP leads to the formation of polycycle 577 in moderate yield (Scheme ).…”

Section: Synthetic Applications Of Pentavalent 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 Pentavalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…Iminoquinones constitute the core structures of many naturally occurring compounds and display important antineoplastic, antifungal, and antibacterial activities ( Figure 1) [1][2][3][4]. Commonly used approaches for the construction of iminoquinones include (i) metal catalysis [5][6][7], (ii) photosynthesis by UV lamps and photosensitizers [7], (iii) 2-iodoxybenzoic acid [IBX, 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide] oxidation [8,9], and (iv) Dess-Martin periodinane [DMP, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one]-mediated oxidative reaction [10]. Although the aforementioned elegant methods appear to be general and efficient, further development of the low-cost and eco-friendly methods that allow the facile assembly of highly functionalized iminoquinone from readily available and simple starting materials is still required, because they have wide range of applications in medicine and biology.…”

Section: Introductionmentioning

confidence: 99%

Photooxygenations and Self-Sensitizations of Naphthylamines: Efficient Access to Iminoquinones

Wei

Tang

Zhong

et al. 2018

Journal of Chemistry

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A series of spiro [fluorene-9,7′-dibenzo[c,h]acridine]-5′-one (SFDBAO) derivatives have been concisely and cleanly obtained by exposure to sunlight without external photosensitizers in the higher yields than that when using a UV lamp. An interesting autocatalyst and self-sensitive procedure have been proposed to explain the effective photooxygenation. SFDBAO derivatives exhibit the continuous π-stacks in single-crystal and electron-withdraw properties with red light-emitting and photovoltaic properties.

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“…Simple p -iminoquinones that are not linked through a fused five-membered ring are isolable. − The instability of 51 appeared to derive from the presence of a low energy pathway for aromatization. Indeed, this pathway has been exploited as a means to access highly substituted hydroxyindole derivatives. − We postulated that the first step in this pathway (tautomerization) could be blocked by the installation of a quaternary center within the six-membered ring of 51 .…”

Section: Formation Of the Tetracyclic Imine 56 As A Means To Circumve...mentioning

confidence: 99%

Substrate-Modified Functional Group Reactivity: Hasubanan and Acutumine Alkaloid Syntheses

King

Herzon

2014

J. Org. Chem.

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Functional group taxonomy provides a powerful conceptual framework to classify and predict the chemical reactivity of molecular structures. These principals are most effective in monofunctional settings, wherein individual functional groups can be analyzed without complications. In more complex settings, the predictive value of these analyses decreases as alternative reaction pathways, promoted by neighboring substituents and aggregate molecular properties, emerge. We refer to this phenomenon as substrate-modified functional group reactivity. In this Perspective, we explain how substrate-modified functional group reactivity molded our synthetic routes to the hasubanan and acutumine alkaloids. These investigations underscore the potential for discovery and insight that can only be gained by studying the reactivity of complex multifunctional structures.

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A New Method for the Synthesis of Iminoquinones via DMP-Mediated Oxidative Reaction

Cited by 10 publications

References 17 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Photooxygenations and Self-Sensitizations of Naphthylamines: Efficient Access to Iminoquinones

Substrate-Modified Functional Group Reactivity: Hasubanan and Acutumine Alkaloid Syntheses

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