Reaction between isocyanides and nitrostyrenes in water: a novel and efficient synthesis of 5-(alkylamino)-4-aryl-3-isoxazolecarboxamides

Adib, Mehdi; Mahdavi, Mohammad; Malihi, Farzad; Zhu, Long‐Guan; Bijanzadeh, Hamid Reza

doi:10.1016/j.tetlet.2009.09.069

Cited by 26 publications

(3 citation statements)

References 40 publications

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“…of an isocyanide 371 with nitrostyrenes 40 in water at 80 C, 5-(alkylamino)-4-aryl-3-isoxazolecarboxamides 372 could be obtained in 83-93% isolated yields (Scheme 128). 242 This protocol is well tolerated for aromatic and heteroaromatic nitroalkenes.…”

Section: And Benzene Ring In 127bmentioning

confidence: 99%

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

2014

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The applications of nitroalkenes in the synthesis of three-to five-membered O, N and S-heterocycles, including natural products are investigated in this review. These heterocyclic compounds were synthesized from nitroalkenes with a variety of substituents at the a and b-positions and those that were part of common and medium rings via a wide variety of reactions such as Michael addition reactions, epoxidation, [3 + 2] cycloaddition and many cascade/domino/tandem reactions. In addition, the potential of nitroalkenes to take part in multi-component and cascade reactions, particularly, in diastereo-and enantioselective versions is reviewed. The high reactivity of nitroalkenes and their potential to coordinate with the metal catalysts as well as organocatalysts signify them as efficient precursors in synthetic organic chemistry. Also, the flexibility of the nitro group in functional group manipulations has expanded the scope of the nitro group, in general, and nitroalkenes, in particular, in organic synthesis.

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Section: And Benzene Ring In 127bmentioning

confidence: 99%

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

2014

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“…Of particular interest is the synthesis of 5-aminoisoxazoles and their N-heterocyclic analogues, because they exhibit a variety of medicinal properties. 67 Substituted isoxazoles decorated with either 3-carboxamide or 5-amino substitutions display antiepileptic, antifungal, insecticidal properties, etc. In this regard, Adib and co-workers described an efficient synthetic route towards 5-alkylamino-4-aryl-3-isoxazole carboxamides 166 through a formal [4+1] cycloaddition reactions of nitrostyrenes 165 and functionalized isocyanide 1 in 80-93% yields (Scheme 55).…”

Section: Nitro-olefinsmentioning

confidence: 99%

“…In this regard, Adib and co-workers described an efficient synthetic route towards 5-alkylamino-4-aryl-3-isoxazole carboxamides 166 through a formal [4+1] cycloaddition reactions of nitrostyrenes 165 and functionalized isocyanide 1 in 80-93% yields (Scheme 55). 67 The reaction proceeded via the nucleophilic attack of isocyanides on nitroolefins 165 to generate nitronate intermediate I, followed by intramolecular cyclization to afford 4,5-dihydroisoxazolium-N-oxide intermediate II. The resulting intermediate II upon a [1,3-H] shift generated the another intermediate isoxazolium-Noxide III, which upon reaction with another molecule of isocyanide followed by rearrangement afforded 5-(alkylamino)-4-aryl-3isoxazole carboxamides 166.…”

Section: Nitro-olefinsmentioning

confidence: 99%

Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs)

et al. 2016

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The advent of cycloaddition reactions in the synthesis of heterocycles and their ever burgeoning applications in the fields of material chemistry, catalysis and drugs have been a profound scientific development. In particular, isocyanide based cycloaddition reactions have been harbingers of an exciting new chapter in the realms of organic synthesis. The emergence of numerous synthetic protocols utilizing formal cycloaddition of isocyanides with conjugated heterodienes has unleashed countless opportunities to design and synthesize diverse heterocyclic scaffolds. To date, there has not been any exclusive review on a formal [4+1] cycloaddition involving isocyanides. The present review highlights the journey of formal [4+1] cycloaddition reactions of isocyanides with diverse electrophilic substrates viz. oxadienes, azadienes, thioacyl imines, alkylidene amides, alkylidene hydrazines, α,β-unsaturated nitro compounds, α-thioxothioamides, nitroso alkenes, acyl imines, vinyl ketenes, vinyl isocyanates, etc. to afford functionalized pyrroles, imidazoles, furans, oxazoles, pyrazoles, etc.

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Molecular Rearrangements: Part 2

Coxon

Organic Reaction Mechanisms· 2005

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Reaction between isocyanides and nitrostyrenes in water: a novel and efficient synthesis of 5-(alkylamino)-4-aryl-3-isoxazolecarboxamides

Cited by 26 publications

References 40 publications

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs)

Molecular Rearrangements: Part 2

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