Hexacarbonylmolybdenum-induced reaction of isoxazoles. Cycloaddition of isoxazoles with acetylenic esters and related reactions.

スポンサーリンク

概要

• 論文の詳細を見る

• In the presence of hexacarbonylmolybdenum, substituted isoxazoles undergo a cycloaddition reaction with dimethyl acetylenedicarboxylate across the C-4–C-5 bond to give 3,4-bis(methoxycarbonyl)pyridine derivatives. In a similar cycloadition of isoxazoles with methyl propiolate, 4-(methoxycarbonyl)pyridine derivatives were also obtained. The β-carbon atom of methyl propiolate could intervene in the bonding with the C-5 position of the isoxazoles regioselectively. A mechanism involving a complexed 2-oxa-3-azabicyclo[3.2.0]hepta-3,6-diene derivative and the subsequent N–O and C-1–C-5 bond cleavage leading to a complexed (β-keto vinyl)nitrene intermediate is proposed for the formation of pyridine derivatives. In order to clarify the mechanistic aspect, the reaction of 4-phenyl-2-oxa-3-azabicyclo[3.2.0]hepta-3,6-diene and its related compounds were also studied to give pyridine derivatives.

• 公益社団法人 日本化学会の論文

著者

• Nitta Makoto

  Department Of Applied Pharmacology Toyama Medical And Pharmaceutical University

• Kobayashi Tomoshige

  Department Of Chemistry Faculty Of Science Shinshu University

関連論文

• Pharmacological and Immunohistochemical Characterization of a Mouse Model of Acute Herpetic Pain
• Roles of luteinizing hormone/chorionic gonadotropin receptor in anchorage-dependent and -independent growth in human ovarian surface epithelial cell lines
• Norbornadiene-Fused Heterocycles: Syntheses and Cycloaddition Reactions of 2-Aryl-4,7-dihydro-4,7-methano-2H-isoindoles and 4,7-Dihydro-4,7-methanoisobenzofuran
• Neighboring Group Participation by Heteroaromatic Rings : The Wagner-Meerwein Type Skeletal Rearrangement in the Electrophilic Addition Reactions of Norbornadiene-Fused Furans, Pyrroles, and Thiophenes
• Oxidizing Ability of a Series of (Tropon-2-ylimino)pnictoranes (Pnictogen=P, As, Sb, and Bi) toward Some Alcohols
• Synthesis and Properties of α, α-Bis(heteroazulen-3-yl)-1, 4-benzoquinonemethides
• The Effect of Fused Rings on the Spectral and Electrochemical Properties of Bis-Fused 1, 4-Diacetyl-1, 4-dihydropyrazines
• Norbornadiene-Fused Heterocycles : Synthesis of 5,8-Dihydro-5,8-methanophthalazines and Regioselective Ring Cleavage and Skeletal Rearrangement of 6,7-Epoxy-5,6,7,8-tetrahydro-5,8-methanophthalazine 2-Oxides in Trifluoroacetic Acid
• Norbornadiene-Fused Heterocycles : Synthesis and Bromination Reaction of 5,8-Dihydro-5,8-methanoquinoxaline Derivatives
• Cycloadditions of constrained dicyclopropylethylenes and divinylcyclopropanes with tetracyanoethylene.
• Preparation, 1,3-dipolar cycloaddition, and thermal and photochemical reactions of 3,5-exo- and 3,5-endo-7-methylene-4-azateracyclo[4.2.1.0.2,803,5]nona-9-ones.
• Thermal rearrangements of 1,5-dimethyl- and 1,3,5-trimethyl-8-vinyl-6-methylenetricyclo[3.2.1.02,7]oct-3-en-8-ol and their alkoxides.
• Hexacarbonylmolybdenum-induced N-N bond cleavage of pyrazoles. Conversion of 1-acylpyrazoles to pyrimidines.
• Acid-Induced Dimerization Reactions of N-(Diphenylphosphinyl)-2-propenimines Leading to Pyridine Derivatives.
• On the reaction of N-(diphenylphosphinyl)-1-phenylethanimine with aromatic aldehydes giving 4-aryl-2,6-diphenylpyridine derivatives.
• The solvomercuration, bromination, and related reactions of 1,5-dimethyl-6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds.
• On the reaction of N-vinyliminophosphoranes. 9. The synthesis and reaction of N-(1,3,5-cycloheptatrienyl)iminophosphoranes to provide a novel route to 1-azaazulenes.
• Preparation of novel N-vinyl-, N-(1-butylvinyl)-, and N-(1-methyl-1-pentenyl)iminotriphenylphosphoranes and their reactions with .ALPHA.,.BETA.-unsaturated ketones.
• The preparation and photoreation of spiro(oxirane-2,6'-tricyclo(3.2.1.02,7)oct(3)en)-8'-ones. An intramolecular cycloaddition of photochemically generated ketene with the epoxide ring.
• Photocycloadditions of benzophenone with 6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds. Di-.PI.-methane photorearrangement of the primary photocycloadducts.
• Stereoelectronic and homoconjugative effect of stereoselectivity. The addition of dichlorocarbene to 1,5-dimethyl-6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds.
• Nonacarbonyldiiron-, pentacarbonyliron-, or hexacarbonylmolybdenum-induced reacions of 4,5-polymethylene-substituted 2-isoxazolines.
• Metal carbonyl-induced N-O bond cleavage of the oxime group.
• Hexacarbonylmolybdenum-induced reaction of isoxazoles. Cycloaddition of isoxazoles with acetylenic esters and related reactions.
• Deoximation of oxime O-acetates, oximes, and oxime ethers by nonacarbonyldiiron or pentacarbonyliron. An electronic effect for the N-O bond cleavage.
• Synthesis and properties of the (n)(2,5)pyridinophane ring system.
• The reaction of (Z)-2-(3-oxo-1-propenyl)-2H-azirine derivative with molybdenum carbonyl complexes.
• On the reaction of N-vinyliminophosphoranes. Part 10. On the reaction of N-vinyliminophosphoranes with 2,4,6-cyclooctatrienone. Intermediate formation of 8-azabicyclo[5.3.1]undeca-2,4,7,9-tetraene ring system.
• The reaction of N-(vinylimino)phosphoranes. Part 13. On the reaction of N-(3-oxo-2-cyclohexenyl)imino)triphenylphosphorane with .ALPHA.-bromo ketones and .ALPHA.,.BETA.-unsaturated ketones.
• Nonacarbonyldiiron-induced reaction of 3-azido-1,2,3-triphenyl-cyclopropene and 4,5,6-triphenyl-1,2,3-triazine.
• A novel formation of phenyl-substituted pyridines by the reaction of N-(diphenylphosphinyl)-1-azaallyl anions with .ALPHA.,.BETA.-unsaturated carbonyl compounds. A new synthetic equivalent of primary vinylamines.

もっと見る 閉じる

スポンサーリンク