Action de l'acide fluorhydrique sur les azirines : synthèse d'α-fluorocétones et de difluoroamines - étude de l'orientation de la réaction

Alvernhe, G.; Lacombe, Sylvie; Laurent, A.

doi:10.1016/s0040-4039(00)92739-4

Cited by 32 publications

(2 citation statements)

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“…It was found that water [37], Brønsted [44,48] and Lewis acids [40–41 43] facilitate the formation of pyrazine derivatives. 2 H -Azirines undergo ring opening on electronic excitation to give nitrile ylides [50].…”

Section: Resultsmentioning

confidence: 99%

“…Different mechanisms of dimerization were assumed, such as formation and dimerization of nitrile ylides [ 37 , 40 ], hydrolysis to α-aminoketenes followed by condensation [ 37 , 41 ], intermediate formation of metal complexes in the reaction mediated by metals [ 41 , 43 , 46 ]. It was found that water [ 37 ], Brønsted [ 44 , 48 ] and Lewis acids [ 40 – 41 43 ] facilitate the formation of pyrazine derivatives. 2 H -Azirines undergo ring opening on electronic excitation to give nitrile ylides [ 50 ].…”

Section: Resultsmentioning

confidence: 99%

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Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems

Khlebnikov¹,

Новиков²,

Pakal’nis³

et al. 2014

Beilstein J. Org. Chem.

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Summary3-Aryl-2H-azirines react with acylketenes, generated by thermolysis of 5-arylfuran-2,3-diones, to give bridged 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-diones and/or ortho-fused 6,6a,12,12a-tetrahydrobis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine-4,10-diones. The latter compounds, with a new heterocyclic skeleton, are the result of the coupling of two molecules of azirine and two molecules of acylketene and can be prepared only from 3-aryl-2H-azirines having no electron-withdrawing groups in the aryl substituent. Calculations at the DFT B3LYP/6-31G(d) level for the various routes of bis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition of the latter to two molecules of acylketenes.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems

Khlebnikov¹,

Новиков²,

Pakal’nis³

et al. 2014

Beilstein J. Org. Chem.

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Azirines

Nair¹

1983

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The Formation of the C  F Bond: The Last Twelve Years

Rozen

2009

Patai's Chemistry of Functional Groups

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Introduction Nucleophilic Fluorinating Reagents Electrophilic Fluorinating Reagents Synthesis of Compounds Containing The 18 F Isotope For Use In Positron‐Emitting Tomography Recent Reviews on Selective Fluorination Methods

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Action de l'acide fluorhydrique sur les azirines : synthèse d'α-fluorocétones et de difluoroamines - étude de l'orientation de la réaction

Cited by 32 publications

References 3 publications

Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems

Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems

Azirines

The Formation of the C  F Bond: The Last Twelve Years

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