A convenient synthesis of N -vinyl enamides via the lithiation and ring-opening reaction of 2-phenyl-2-oxazolines

Xu, Yi; Liu, Xiaoyu; Wang, Ziqi; Tang, Liang‐Fu

doi:10.1016/j.tetlet.2017.03.080

Cited by 4 publications

(3 citation statements)

References 46 publications

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“…The authors have cited additional references within the Supporting Information. [22][23][24][25][26][27][28][29]…”

Section: Supporting Informationmentioning

confidence: 99%

Photoredox Catalytic Access to N,O‐Acetals from Enamides by Means of Electron‐Poor Perylene Bisimides

Steuernagel,

Rombach,

Wagenknecht

2024

Chemistry A European J

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N,O‐acetals are found as structural motif in natural products and are important synthetic precursors for N‐acylimines as building blocks in organic synthesis for C‐C‐bond formation and amines. For the synthesis of N,O‐acetals, an acid‐, base‐ and metal‐free catalytic method is reported applying N,N‐di‐(2,6‐diisopropyl)‐1,7‐dicyano‐perylen‐3,4,9,10‐tetracarboxylic acid imide and N,N‐di‐(2,6‐diisopropyl)‐1,6,7,12‐tetrabromo‐2,5,8,11‐tetracyano‐perylen‐3,4,9,10‐tetracarboxylic acid imide as extremely electron‐deficient photocatalysts. The first perylene bisimide highly selectively photocatalyzes the formation of the N,O‐acetals as products in high yields, and the second and more electron‐deficient perylene bisimide allows these reactions without thiophenol as H‐atom transfer reagent. Calculated electron density maps support this. The reaction scope comprises different substituents at the nitrogen of the enamides and different alcohols as starting material. Dehydroalanines are converted to non‐natural amino acids that shows the usefulness of this method for organic and medicinal chemistry.

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“…The authors have cited additional references within the Supporting Information. [22][23][24][25][26][27][28][29]…”

Section: Supporting Informationmentioning

confidence: 99%

Photoredox Catalytic Access to N,O‐Acetals from Enamides by Means of Electron‐Poor Perylene Bisimides

Steuernagel,

Rombach,

Wagenknecht

2024

Chemistry A European J

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“…O-Acylhydroxylamines 3 were synthesized from the corresponding NH 2 OH derivatives by reported methods. 9 Enamides 2c 11 and 2e 12 were synthesized according to reported methods. fac-Ir(ppy) 3 was purchased from Adamas-beta.…”

Section: Special Topic Syn Thesismentioning

confidence: 99%

Photoredox-Catalyzed Radical Relay Reaction Toward Functionalized Vicinal Diamines

2018

Synthesis

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A strategy has been described to synthesize β,γ-diaminoketones. This strategy is enabled by photoredox-catalyzed and nitrogen-centered radical-triggered cascade reactions of styrenes, enamides, and O-acylhydroxylamines in DMSO. Four bonds (one C–C, one C–N, and two C–O) are constructed in a single operation. Various functionalized vicinal diamines have been furnished by the radical relay reaction.

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“…[2] Enamides can participate in a variety of reactions, such as transition metal catalysis, various total synthesis, enantiomer synthesis, and photochemistry etc. [3] The reported methods for preparing N-vinyl benzamide include i) the reaction of benzoyl chloride with Nvinylformamide; [3c,d,4] ii) the lithiation and ring-opening reaction of 2-phenyl-4,5-dihydrooxazole [5] ; iii) the elimination of thiophenol from N- (2-(phenylthio)ethyl)benzamide; [6] iv) the direct Nvinylation of benzamide using vinyltrimethoxysilane, [7] potassium vinyltrifluoroborate, [8] vinyl bromide, [9] or vinyl acetate [10] as reagents (Scheme 1). However, these methods require more complicated substrates and difficult-to-obtain reagents, and the use of transition metal catalysts and harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Selective N‐Monovinylation of Primary Aromatic Amides Using Calcium Carbide as an Alkyne Source

et al. 2022

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An efficient method for the selective N‐monovinylation of primary aromatic amides using calcium carbide as an alkyne source is described. A series of N‐vinylbenzamides (enamides) were readily synthesized by this strategy. The salient features for this protocol are the use of inexpensive, easy‐to‐handle solid alkyne source, high chemoselectivity, transition metal catalyst‐free, good functional group tolerance, and simple work‐up procedures. These reactions can also be extended to the gram‐scale level.

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A convenient synthesis of N -vinyl enamides via the lithiation and ring-opening reaction of 2-phenyl-2-oxazolines

Cited by 4 publications

References 46 publications

Photoredox Catalytic Access to N,O‐Acetals from Enamides by Means of Electron‐Poor Perylene Bisimides

Photoredox Catalytic Access to N,O‐Acetals from Enamides by Means of Electron‐Poor Perylene Bisimides

Photoredox-Catalyzed Radical Relay Reaction Toward Functionalized Vicinal Diamines

Selective N‐Monovinylation of Primary Aromatic Amides Using Calcium Carbide as an Alkyne Source

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