Atom‐Economic Silver‐Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones

Liang, Hong‐Wen; Yang, Zhen; Jiang, Kun; Ye, Ying; Wei, Ye

doi:10.1002/ange.201801363

Cited by 6 publications

(3 citation statements)

References 79 publications

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“…For 1 H and 13 C spectra data of 1a, 1b, 1e−i, and 1o, one can refer to the published document. 9 For 1 H and 13 C spectra data of 1m, one can refer to the published document. 14 For 1 H and 13 C spectra data of 1p, one can refer to the published document.…”

Section: Methodsmentioning

confidence: 99%

“…8 In 2018, Wei's group successfully realized the silver catalyzed synthesis of pyrimidinedione derivates utilizing isocyanide and isoxazolone (Scheme 1e). 9 The highlight is that the C and N atoms of the isocyanide are simultaneously involved in the ring expansion reaction while possessing good substrate universality. However, attempts to use tert-butyl isocyanide led to the product having less than 10% yield.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Palladium Catalyzed Insertion Reaction of Isocyanides with 3-Arylisoxazol-5(4H)-ones: Synthesis of 4-Aminomethylidene Isoxazolone Derivates

Zhu

Wang

et al. 2019

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Palladium Catalyzed Insertion Reaction of Isocyanides with 3-Arylisoxazol-5(4H)-ones: Synthesis of 4-Aminomethylidene Isoxazolone Derivates

Zhu

Wang

et al. 2019

J. Org. Chem.

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“…Recently, Wei and co‐workers reported the syntheses of pyrimidinediones via the Ag 2 O catalyzed difunctionalization of an isocyano group with cyclic oximes (eq 4, Scheme 1). [21] Inspired by their work and considering that dioxazolones and cyclic oximes have structural similarities, it was speculated that the reactions between dioxazolones and isocyanides may proceed by silver catalysis. Herein, the one‐pot syntheses of a series of N ‐acylureas via silver‐catalyzed acyl nitrene transfer reactions involving dioxazolones, isocyanides, and water are reported for the first time (eq 5, Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

Silver‐Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N‐Acylureas

Yang

Xu²,

Chen

et al. 2020

Eur J Org Chem

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Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silvercatalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag 2 O to afford a series of N-acylureas in moderate to good yields. The incorporation of an amide moiety into a molecule is of considerable importance because of the presence of this substructure in many biologically active molecules and natural products. [1] In the late 1960s, 1,4,2-dioxazol-5-ones (dioxazolones) 1 were identified by Sauer and Mayer as safe alternatives to acyl azides for N-acyl nitrene formation. [2] Owing to their low cost, ready availability, and environmental friendliness, 1,4,2dioxazol-5-ones have been extensively studied as amidating reagents in the past several years. In 2009, Dubé et al. published a pioneering method to prepare isocyanates by employing 1,4,2-dioxazol-5-ones. [3] Later, Bolm and co-workers reported the first light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by the decarboxylation of 1,4,2dioxazol-5-ones (eq 1, Scheme 1). [4] Subsequently, dioxazolones were reported as amidating reagents for Rh-catalyzed CÀ H amidation by the Chang group. [5] Thereafter, a series of Rh-, [6] Co-, [7] and Ir-catalyzed [8] CÀ H amidation reactions were developed using this amidating reagent (eq 2, Scheme 1). Furthermore, Li, Zhu, Glorius, Ackermann, and other research groups described the cascade C À H amidation and cyclization reactions for the syntheses of various heterocycles. [9] Bruin and co-workers recently reported the fast N-acyl amidations via Cucatalyzed three-component reaction of aryl acetylenes, amines, and 1,4,2-dioxazol-5-ones (eq 3, Scheme 1). [10] However, to the best of our knowledge, the silver-catalyzed reaction of 1,4,2dioxazol-5-one via acyl nitrene has not been reported in the literature.

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Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3‐Oxazin‐6‐One Derivatives

Zhu

Wan

et al. 2020

Adv Synth Catal

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A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring‐opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation‐induced emission properties with relatively high solid‐state emission efficiencies.

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Atom‐Economic Silver‐Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones

Cited by 6 publications

References 79 publications

Palladium Catalyzed Insertion Reaction of Isocyanides with 3-Arylisoxazol-5(4H)-ones: Synthesis of 4-Aminomethylidene Isoxazolone Derivates

Palladium Catalyzed Insertion Reaction of Isocyanides with 3-Arylisoxazol-5(4H)-ones: Synthesis of 4-Aminomethylidene Isoxazolone Derivates

Silver‐Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N‐Acylureas

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3‐Oxazin‐6‐One Derivatives

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