Efficient cleavage of the N–O bond of 3,6-dihydro-1,2-oxazines mediated by some α-hetero substituted carbonyl compounds in mild conditions

Galvani, Gilles; Calvet, Géraldine; Blanchard, Nicolas; Kouklovsky, Cyrille

doi:10.1039/b718787d

Cited by 23 publications

(9 citation statements)

References 40 publications

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“…Common reagents that facilitate cleavage of the N À O bond include molybdenumhexacarbonyl ([Mo(CO) 6 ]), [96,97] zinc in acetic acid, catalytic hydrogenation, samarium diiodide, [98,99] and titanocene(III) chloride. [100] Other methods for reduction of the NÀO bond include the use of photochemical, [101] enzymatic, [102] and other chemical [103] processes.…”

Section: Nào Bond Cleavagementioning

confidence: 99%

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Bodnar¹,

2011

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Organic transformations that result in the formation of multiple covalent bonds within the same reaction are some of the most powerful tools in synthetic organic chemistry. Nitrosocarbonyl hetero-Diels–Alder (HDA) reactions allow for the simultaneous stereospecific introduction of carbon–nitrogen and carbon–oxygen bonds in one synthetic step, and provide direct access to 3,6-dihydro-1,2-oxazines. This Review describes the development of the nitrosocarbonyl HDA reaction and the utility of the resulting oxazine ring in the synthesis of a variety of important, biologically active molecules.

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Section: Nào Bond Cleavagementioning

confidence: 99%

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Bodnar¹,

2011

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“…R f =0.45 (petroleum ether/ethyl acetate 2:1); 1 H NMR (400 MHz, CDCl 3 ): δ= 8.18 (d, J= 8.8 Hz, 2 H), 7.52 (d, J= 8.8 Hz, 2 H), 6.94 (dd, J= 15.6, 11.8 Hz, 1 H), 6.60 (d, J= 15.6 Hz, 1 H), 6.48 (dd, J= 15.2, 11.8 Hz, 1 H), 6.14–6.08 (m, 1 H), 4.31 ppm (d, J= 4.4 Hz, 2 H). The data were in agreement with the literature …”

Section: Methodsmentioning

confidence: 99%

Facile Preparation of α‐Cyano‐α,ω‐Diaryloligovinylenes: A New Class of Color‐Tunable Solid Emitters

Zhang

et al. 2015

Chemistry An Asian Journal

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An efficient Knoevenagel condensation reaction was used to construct a series of α-cyano-α,ω-diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties, we found that the diene structure showed superior solid-state luminescence. Furthermore, the emission color could be adjusted by introducing donor or acceptor functional groups at the terminal aryl groups. Full-color emission in the visible region can be achieved by adding different functional groups to the α-cyano-α,ω-diaryldivinylene moiety. The structure-property relationships were elucidated and some observations such as the substitution position effects were discussed. These compounds have potential applications as full-color solid emissive candidates in material science and their simple structures allow them to be easily modified resulting in further interesting properties.

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“…Gängige Reagentien und Verfahren, die die N-O-Bindungsspaltung erleichtern, sind Molybdänhexacarbonyl ([Mo(CO) 6 ]), [96,97] Zink in Essigsäure, die katalytische Hydrierung, Samariumdiiodid [98,99] und Titanocen(III)-chlorid. [100] Weitere Methoden zur reduktiven Spaltung der N-O-Bindung nutzen photochemische [101] und enzymatische [102] sowie andere chemische [103]…”

Section: Spaltung Der N-o-bindungunclassified

Hetero‐Diels‐Alder‐Reaktionen von Nitrosocarbonylverbindungen als nützliches Verfahren in der organischen Synthese

Bodnar¹,

Miller

2011

Angewandte Chemie

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Organische Transformationen, die in einem einzigen Reaktionsschritt mehrere kovalente Bindungen aufbauen, zählen zu den leistungsfähigsten Verfahren in der organischen Synthese. Hetero‐Diels‐Alder(HDA)‐Reaktionen von Nitrosocarbonylverbindungen ermöglichen die stereospezifische Einführung von Kohlenstoff‐Stickstoff‐ und Kohlenstoff‐Sauerstoff‐Bindungen in einem einzigen Syntheseschritt und bieten einen direkten Zugang zu 3,6‐Dihydro‐1,2‐oxazinen. In diesem Aufsatz werden die Entwicklung der Nitrosocarbonyl‐HDA‐Reaktion und der Nutzen der daraus erhältlichen Oxazinringe bei der Synthese verschiedener wichtiger biologisch aktiver Verbindungen beschrieben.

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Efficient cleavage of the N–O bond of 3,6-dihydro-1,2-oxazines mediated by some α-hetero substituted carbonyl compounds in mild conditions

Cited by 23 publications

References 40 publications

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Facile Preparation of α‐Cyano‐α,ω‐Diaryloligovinylenes: A New Class of Color‐Tunable Solid Emitters

Hetero‐Diels‐Alder‐Reaktionen von Nitrosocarbonylverbindungen als nützliches Verfahren in der organischen Synthese

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