Reaction of Halogenated Cyclopropanes and Nitrosyl Cation:  Preparation of Isoxazoles

Lin, Shaw‐Tao; Kuo, S.‐H.; Yang, Fu-May

doi:10.1021/jo962297i

Cited by 42 publications

(19 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97. Isoxazole derivatives exhibit anticonvulsant, antibacterial, antiasthmatic, and other pharmacological activities (Lin et al, 1997). Isoxazoles are typically prepared by the reaction of nitrile oxides with alkynes (Hanson & Mohamed, 1997) or olefine.…”

Section: Data Collectionmentioning

confidence: 99%

1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

Xie¹,

Mo²,

Mo³

et al. 2007

Acta Cryst E

View full text Add to dashboard Cite

show abstract

Section: Data Collectionmentioning

confidence: 99%

1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

Xie¹,

Mo²,

Mo³

et al. 2007

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…[8][9][10][11]34,35 Two mechanistic rationales could be therefore postulated. The first step of the ionic pathway involves the electrophilic attack of NO + and the opening of the three-membered ring (path A, Scheme 4) resulting in the formation of the intermediate II.…”

mentioning

confidence: 99%

Three-Component Heterocyclization of gem-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine N-Oxides

et al. 2012

View full text Add to dashboard Cite

Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.

show abstract

“…The arylcyclopropanes studied in these transformations have been either phenylcyclopropanes [7][8][9] or benzylcyclopropanes [10] substituted in the aromatic ring or have contained only alkyl and aryl groups [11,12] or halogen atoms [13,14] as the second substituent in the cyclopropane ring. Hence, the possible series of substituted 4,5-dihydroisoxazoles and corresponding isoxazoles obtained by this method has been limited to heterocycles with nonfunctional substituents.…”

mentioning

confidence: 99%

Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles

Каджаева

Трофимова

Федотов

et al. 2009

Chem Heterocycl Comp

View full text Add to dashboard Cite

Esters of 2-arylcyclopropanecarboxylic acids react with nitrous acid generated in situ with regioselective insertion of the nitrosyl cation into the cyclopropane ring. Depending on the substrate/nitrosylating agent ratio, the reaction proceeds with the formation of either aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles or the corresponding isoxazoles. The nature and position of the substituents in the aromatic ring of the starting 2-arylcyclopropanecarboxylic acid esters affect the reaction rate but have no effect on the regioselectivity of the attack by the nitrosyl cation on the three-membered ring. A dependence of the reactivity of isomeric substrates on their stereochemistry and position of the nitro group in the aromatic ring is noted for 2-and 4-nitrophenyl derivatives of esters of cis-and trans-2-arylcyclopropanecarboxylic acids.Keywords: 5-aryl-3-ethoxycarbonyl-4,5-dihydroisoxazoles, 5-aryl-3-ethoxycarbonylisoxazoles, ethyl esters of 2-arylcyclopropanecarboxylic acids, insertion of the nitrosyl cation into the cyclopropane ring.The reaction of arylcyclopropanes with nitrosylating agents, which proceeds through insertion of the nitrosyl cation or nitrosyl radical into the cyclopropane ring, may be seen as one of the most efficient methods for the synthesis of aryl-substituted 4,5-dihydroisoxazoles and isoxazoles, which are potential pharmaceutical agents and important precursors for the preparation of biologically-active compounds, including natural products [1][2][3][4][5][6].

show abstract

Reaction of Halogenated Cyclopropanes and Nitrosyl Cation: Preparation of Isoxazoles

Cited by 42 publications

References 9 publications

1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

Three-Component Heterocyclization of gem-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine N-Oxides

Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles

Contact Info

Product

Resources

About

Reaction of Halogenated Cyclopropanes and Nitrosyl Cation: Preparation of Isoxazoles

Cited by 42 publications

References 9 publications

1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone

Three-Component Heterocyclization of gem-Bromofluorocyclopropanes with NOBF4: Access to 4-Fluoropyrimidine N-Oxides

Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles

Contact Info

Product

Resources

About

Three-Component Heterocyclization of gem-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine N-Oxides