Palladium-Catalyzed Synthesis of 4-Aminophthalazin-1(2H)-ones by Isocyanide Insertion

Vlaar, TjÃ ̧stil; Ruijter, Eelco; Znabet, Anass; Janssen, Elwin; Kanter, Frans J. J. de; Maes, Bert U. W.; Orru, Romano V. A.

doi:10.1021/ol202784d

Cited by 117 publications

(41 citation statements)

References 35 publications

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“…reported the analogous copper‐catalyzed cross‐coupling of aryl halides with hydrazine 17. A palladium‐catalyzed multicomponent synthesis of aryl hydrazines from hydrazine hydrate has also been developed 18…”

Section: Optimization Of the Reaction Conditionsmentioning

confidence: 99%

Room‐Temperature Hydrohydrazination of Terminal Alkynes Catalyzed by Saturated Abnormal N‐Heterocyclic Carbene–Gold(I) Complexes

Manzano¹,

Wurm

Röminger

et al. 2014

Chemistry A European J

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A number of saturated abnormal N-heterocyclic carbene (NHC) complexes of gold, in combination with KBAr(F) 4 as activator, were successfully applied in the chemoselective addition of hydrazine to alkynes. The reaction proceeds even at room temperature, which was not possible to date with gold catalysts. The reaction can be applied to a number of substituted arylalkynes. With alkylalkynes the yields are low. The saturated abnormal NHC ligands are resistant to isomerization to the saturated normal NHC coordination mode under basic reaction conditions. Under acidic conditions, a simple protonation at the nitrogen atom not neighboring the carbene center was observed and unambiguously characterized by an X-ray crystal-structure analysis. Computational studies confirm that such an isomerization would be highly exothermic, the observed kinetic stability probably results from the need to shift two protons in such a process.

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Section: Optimization Of the Reaction Conditionsmentioning

confidence: 99%

Room‐Temperature Hydrohydrazination of Terminal Alkynes Catalyzed by Saturated Abnormal N‐Heterocyclic Carbene–Gold(I) Complexes

Manzano¹,

Wurm

Röminger

et al. 2014

Chemistry A European J

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“…The replacement of one of the ortho methyl groups on the isocyanide substrate with a chloro or ethyl group was also well tolerated, with the C-H bond of the remaining methyl group reacting selectively to give the desired corresponding indoles 40l and m as single products. The use of an isocyanide substrate bearing only one ortho substituent (i.e., 2,4-dimethylphenyl isocyanide) failed to afford any of the desired product 40n, most likely because of the poor stability of the less hindered isocyanide 93,94) and the flexible conformation of the reaction intermediate.…”

Section: )mentioning

confidence: 99%

Palladium(0)-Catalyzed Benzylic C(sp3)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

Tsukano

2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…(125)]. [174] Only tertiary isonitriles participate, possibly because sterically demanding isonitriles, in combination with the large bidentate Xanthos, are required to prevent the irreversible complexation of the isonitrile to the palladium catalyst. Aryl bromides, iodides and triflates couple equally well but aryl chlorides are inefficient coupling partners.…”

Section: Miscellaneous Isonitrile Condensationsmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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Palladium-Catalyzed Synthesis of 4-Aminophthalazin-1(2H)-ones by Isocyanide Insertion

Abstract: Palladium-catalyzed cross-coupling of a wide range of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion followed by lactamization efficiently affords 4-aminophthalazin-1(2H)-ones that are difficult to obtain regioselectively by classical methods.

Cited by 117 publications

References 35 publications

Room‐Temperature Hydrohydrazination of Terminal Alkynes Catalyzed by Saturated Abnormal N‐Heterocyclic Carbene–Gold(I) Complexes

Room‐Temperature Hydrohydrazination of Terminal Alkynes Catalyzed by Saturated Abnormal N‐Heterocyclic Carbene–Gold(I) Complexes

Palladium(0)-Catalyzed Benzylic C(<i>sp</i><sup>3</sup>)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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