Use of 1,3-Dioxin-4-ones and Related Compounds in Sythesis. XXXVIII. Use of 1,3-Dioxin-4-ones Having a Fluorine or Trifluoromethyl Group at the 5-Position as _π2 Components in [2+2]-Photocycloaddition and Diels-Alder Reactions

スポンサーリンク

概要

• 論文の詳細を見る

• 1,3-Dioxin-4-ones having fluorine or a trifluoromethyl group at the 5-position were used as the _π2 components in Diels-Alder reactions with 1-oxygenated dienes. Use of high-perssure conditions was the essential requisite. While the 5-flurodioxinones were photolabile, the corresponding trifluoromethyl derivatives participated as the enone components in [2+2]photocycloaddition to alkenes, Ring-opening reactions of these adducts by acetal bond cleavage gave cyclobutanes and cyclohexanes. Diels-Alder reactions of the fluorinated homochiral dioxinones having l-menthone at the acetal position with Danishefsky diene proceeded in a completely diastereoselective manner to give single adducts.

• 公益社団法人日本薬学会の論文
• 1992-09-25

著者

• 佐藤 雅之

  静岡県立大学薬学部

• 金子 主税

  東北大学

• 金子 主税

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 佐藤 雅之

  Pharmaceutical Institute, Tohoku University

• 片桐 信弥

  Pharmaceutical Institute, Tohoku University

• 岩岡 友保

  Pharmaceutical Institute, Tohoku University

• 片桐 信弥

  Health Sci. Univ. Hokkaido Hokkaido Jpn

• 片桐 信弥

  Pharmaceutical Institute Tohoku University

• 岩岡 友保

  Pharmaceutical Institute Tohoku University

• Katagiri N

  Pharmaceutical Institute Tohoku University

関連論文

• A Novel Synthesis of β-Ketothioesters
• A Novel Synthetic Method for Tetronic Acids from 1,3-Dioxin-4-ones via Intra- or Intermolecular Ketene Trapping
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVIII. : Synthesis of Azetidin-2-ones from 1,3-Dioxin-4-ones via 3-Hydroxycarboxamides
• Studies on Amino Acid Derivatives. IX. : Synthesis of Chiral Penam-3-carboxylic Acid and Its Substituted Derivatives
• REDUCTION OF OXIMES OF α-SUBSTITUTED β-KETOESTERS WITH SODIUM CYANOBOROHYDRIDE : STEREOSELECTIVE SYNTHESIS OF 3,4-CIS-SUBSTITUTED AZETIDIN-2-ONES(Communications to the Editor)
• Entstehung von 3-Hydroxyderivaten bei der N-Oxydierung der Chinolinderivate mittels Wasserstoffperoxyds in Eisessig-Losung.
• Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
• Cycloadditions in Syntheses. XXXVII. : Syntheses of 6-Trifluoromethyl-1,2,4-triazines and -1,2,4-triazin-5-ones and Their Pericyclic Reactions with Olefins
• Cycloadditions in Syntheses. XXXI. 2+2 Photocycloaddition of 3-Trifluoromethyl Derivatives of Quinoxalin-2(1H)-one and 1,4-Benzoxazin-2-one to Olefins : Effects of the Trifluoromethyl Group(Organic,Chemical)
• DOUBTS ABOUT THE LIBIT'S METHOD FOR THE SYNTHESIS OF THE "COREY"INTERMEDIATE USING PHOTOCYCLOADDITION AS A KEY STEP
• 菌類代謝産物の研究(第6報)Skyrinの構造について その2
• Endothianin及びRadicalisinのSkyrin及びRugulosinとの同定並びにSkyrinの構造について
• Studies on Ketene and Its Derivatives. XCV. Reaction of Diketene with Acyl Azides
• Reaction of Diketene-Acetone Adduct with Enamines, Ketene Acetals, Vinyl Ethers, and β-Diketones
• Studies on Ketene and Its Derivatives. CXVIII. Nickel- or Palladium-Catalyzed Reaction of Diketene with Organometallics. Synthesis of 3-Substituted 3-Butenoic Acids
• STUDIES ON KETENE AND ITS DERIVATIVES. CXV. REACTION OF DIKETENE WITH ORGANOMETALLICS IN THE PRESENCE OF THE NICKEL- OR PALLADIUM-PHOSPHINE COMPLEX
• REACTION OF METHANE WITH MOLECULAR FLUORINE : AN AB INITIO MO STUDY
• hPIV-1シアリダーゼ阻害活性をもつシアル酸誘導体の合成研究
• 研究開発情報 フルオラス・タグ法による抗シアリダーゼ活性をもつシアル酸誘導体の効率的合成研究
• 学術貢献賞受賞 津田喜典氏の業績
• WHY MOLECULAR FLUORINE ADDS TO ETHYLENES IN A CIS FASHION
• メディシナル・ケミストリーの新しい流れ
• P2-101 水道水中の変異原物質MXの付加体形成に関する研究(環境変異原)
• ケテン化学の新展開:α-オキソケテンの合成と反応
• Addition of Molecular Fluorine to Azlactones : General Synthetic Method of erythro-β-Fluorinated α-Amino Acids
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines : Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst
• Facile Synthesis of 5α-Fluorocholestan-3-one from 4-Cholesten-3-one via Molecular Fluorine Addition and Reductive Defluorination
• Use of 1,3-Dioxin-4-ones and Related Compounds in Sythesis. XXXVIII. Use of 1,3-Dioxin-4-ones Having a Fluorine or Trifluoromethyl Group at the 5-Position as _π2 Components in [2+2]-Photocycloaddition and Diels-Alder Reactions
• l-MENTHYL (2S)-2-PHENYL-3-(p-ANISYL)-(5Z)-BENZYLIDENE-4,6-DIOXO-1,3-OXAZINE-2-CARBOXYLATE : A NEW CHIRAL HETERODIENE AND MICHAEL ACCEPTOR
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis XX. : (6S, 7S, 10R)- and (6R, 7S, 10R)-7-Isopropyl-10-mythyl-4-oxo-1,5-dioxaspiro[5.5]undec-2-enes; Synthesis and Their Use in Enantiomerically Pure Corey Lactone Analogue Synthesis
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVII. : Chiral Spirocyclic 4-Oxo-1,3-dioxin-5-carboxylates : Asymmetric Synthesis of Carbocyclic C-Nucleoside Precursors
• Synthesis of Nucleosides and Their Related Compounds. XII. : Menthyl 2,4-Dioxo-1,3-oxazine-5-carboxylates : New Dienophiles for the Asymmetric Diels-Alder Reaction Directed towards Synthesis of Carbocyclic C-Nucleosides
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis.XVI. : 4-Oxo-1,3-dioxin-5-carboxylic Acids and Related Compounds : Versatile Synthetic Intermediates for the Synthesis of 6-Unsubstituted Six-Membered Heterocyclic Compunds
• キラルな1,3-ジオキシン-4-オン類の不斉有機合成への利用
• 1,3-ジオキシン-4-オン類の合成と有機合成への応用 : 最近の進歩
• A NEW METHOD FOR INTRODUCING THE 2,2-DICHLOROETHYL GROUP AT THE 3 POSITION OP THE 2-QUINOLONE SYSTEM, AND THE SYNTHESIS OF DICTAMNINE(Communication to the Editor)
• Cycloadditions in Syntheses. XXXII. Intramolecular Photocycloaddition of 4-(ω-Alkenyloxy)quinolin-2(1H)-one: Synthesis of 2-Substituted Cyclobuta[c]quinolin-3(4H)-ones(Organic,Chemical)
• Chemical Reactions of Bikaverin
• 新しい反応活性種,ニトロソケテンを経る機能性環状ニトロンの生成と変型アミノ酸合成への展開
• SELECTIVE PROTECTION OF THE PRIMARY HYDROXYL GROUPS OF OXETANOCIN A AND CONFORMATIONAL ANALYSIS OF O-PROTECTED OXETANOCIN A
• 新規ヌクレオシド分子の構築--炭素環ヌクレオシドを中心に(新規合成法の開発) (核酸化学の新展開--新しい機能性分子を求めて) -- (新しい構造と機能を有するヌクレオシドの分子設計)
• EXPLANATION FOR STEREOSELECTIVITY OF THS CIS-DIHYDROXYLATION OF CIS-3,5-DISUBSTITUTED CYCLOPENTENES
• Synthesis of Nucleosides and Related Compounds. XXXIV. Synthesis of 5-Isonitroso-1,3-dioxane-4,6-diones and Their Reactions
• Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4,t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase
• Synthesis of Nucleosides and Related Compounds. XXVI. The Difference in Effects between High Pressure and LiClO_4 for the Diels-Alder Reaction of Cyclopentadiene with Methylenemalonates or O-Acetylisonitrosomalonates
• The Alkylation of 6-Chloropurine with Alcohols by Mitsunobu Reaction
• Synthesis of Nucleosides and Related Compounds. XXII. Carbocyclic Analogues of Thymidine and Related compounds from 2-Azabicyclo[2.2.1]hept-5-en-3-ones
• 超高圧下の有機反応
• Synthesis of Carbocyclic Nucleosides from 2-Azabicyclo[2.2.1]hept-5-en-3-ones : Sodium Borohydride-Mediated Carbon : Nitrogen Bond Cleavage of Five- and Six-Membered Lactams
• Synthesis of Nucleosides and Related Compounds. XVII. Dialkyl 1,3-Dithiethan- and 1,3-Dithiolan-2-ylidenemalonate S-Oxides : Equivalents to Dialkoxycarbonylketenes
• SYNTHESIS OF 9-(t-2,c-3-DIHYDROXYMETHYL-r-1-CYCLOPROPYL)-9H-ADENINE (A LOWER METHYLENE HOMOLOG OF CARBOCYCLIC OXETANOCIN) AND RELATED COMPOUNDS
• HIGHLY STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC ANALOGUES OF OXETANOCIN
• Synthesis of Nucleosides and Related Compounds. XIV. : Diels-Alder Reaction of Di-l-menthyl Acetoxymethylenemalonate with Cyclopentadiene : Effects of High-Pressure and Catalysts upon Asymmetric Induction
• Titanium Tetrachloride-Mediated Diels-Alder Reactions of Cyclopentadiene with Di-l-menthyl Methylenemalonate and Its Acetoxy Derivative as New Chiral Dienophiles for Asymmetric Induction
• Uber eine modifizierte Reissert'sche Reaktion in der Chinolin-1-oxid-Reihe.
• Polarisation der Heterozyklischen Ringe mit aromatischem Charakter. CXXXVII. Bemerkung zur Nitrierung des Pyridin-1-oxydes mittels Acylnitrates und uber 3,5-Dinitropyridin-1-oxyd.
• Uber 2-Hydroxychinolin-1-oxyd.
• Uber eine neue Nitrierung des Chinolin-1-oxydes. (3).
• Nitrierung des 6-Methyl-und 3-Bromchinolin-N-oxydes mit Benzoylnitrat.
• Uber eine neue Nitrierung des Chinolin-N-oxydes. (2).
• Polarisation der heterozyklischen Ringe mit aromatischem Charakter. CXV. Uber eine neue Nitrierung des Chinolin-N-oxydes.
• 炭素-炭素二重結合(特にエノン類)への分子フッ素の付加反応
• 分子フッ素を用いたフッ素化反応と含フッ素生理活性物質合成への応用
• 薬学会賞受賞福本圭一郎氏の業績
• 新反応設計と創薬合成への展開
• "知識は真実ではない"ということ
• Studies on Amino Acid Derivatives. V. Synthesis of Pyridobenzazoles
• A SIMPLE METHOD FOR SYNTHESIZING 7-OXO-4-THIA-1-AZABICYCLO [3. 2. 0]-HEPTANE AND ITS 6-METHYL DERIVATIVES FROM ETHYL CYANOACETATE
• SYNTHESIS OF 4-TRIFLUOROMETHYLAZETIDIN-2-ONES BY A NOVEL 2+2 PHOTOCYCLOADDITION OF 3-TRIFLUOROMETHYL-QUINOXALIN-2-ONE OR-1,4-BENZOXAZIN-2-ONE TO KETENE
• Photoaddition of 4(3H)-Quinazolinone Derivatives to Olefins : Effects of the 2-Substituent
• Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H, 4H-1,3-dioxin-4-ones
• Reaction of 2,2-Dimethyl-1,3-dioxin-4-ones with Imines, Carbodiimides, and Isocyanates
• Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Imines
• Synthesis of 1,3-Dioxin-4-one Derivatives
• Novel Annelation Method to Pyridine and Isoquinoline by Photochemical Means
• Photochemical [2+2] Cycloreversion Reactions of 1,2,2a, 8b-Tetrahydrocyclobuta [c] isoquinolin-4 (3H)-ones
• Synthesis of N-Acylacetoacetamide using 2,2,6-Trimethyl-1,3-dioxin-4-one
• Studies on Ketene and Its Derivatives. CV. Photoreaction of Diketene with sec-Alcohols
• Synthesis of Methylpyridine Derivatives. XXXIV. Condensation of Acetoacetamide with Ketones to form Pyridone Derivatives
• Studies on Ketene and Its Derivatives. XCII. Reaction of Diketene with Benzaldehyde, Cinnamaldehyde, and β-Phenylcinnamaldehyde
• Studies on Ketene and Its Derivatives. LXXXVII. Photoreaction of Diketene with 3-Acetoxy-5,5-dimethyl-2-cyclohexenone
• Studies on Ketene and Its Derivatives. LXIX. Reaction of Diketene with Hydrazobenzenes
• Studies on Ketene and Its Derivatives. LXVII. Photoreaction of Benzophenone and Benzaldehyde with Diketene
• ケテンおよびその誘導体の研究(第52報)ジケテンとα(β)-アミノニトリルとの反応
• ケテンおよびその誘導体の研究(第51報))α-アミノ酸アミドとジケテンとの反応
• NOVEL METHODS FOR INTRODUCING A TWO-CARBON UNIT AT EITHER THE 3- OR 4-POSITION OF THE ISOQUINOLONE RING BY MEANS OF PHOTO[2+2]CYCLOADDITION REACTION
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XIII. : Synthesis of 5-Halo-1,3-dioxin-4-ones and Their Conversion to 5-Alkyl Derivatives
• Cycloadditions in Syntheses. XXVI. : 1,2-Dihydrocyclobuta[b]-naphthalene-3,8-diones : Synthesis by Photochemical Means and Their Reactions via 2,3-Dimethylene-1,4-dioxo-1,2,3,4-tetrahydronaphthalenes
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XI. : 2,2-Dimethyl-1,3-dioxin-4-one as a Synthetic Equivalent of Formylketene : Synthesis of Heterocyclic Compounds
• Cycloadditions in Syntheses. XXIV. 1,2-Dihydrocyclobut [c] isoquinoline
• ノルボルネンはなぜ選択的にエキソ面で反応を起こすのか (1992年の化学-11-)
• Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Isoquinolinium and Pyridinium Ylides
• 化学反応の立体選択性は何によって決まるか-2-反結合性軌道の役割
• 化学反応の立体選択性は何によって決まるか-1-反結合性軌道の役割
• 1, 3-ジオキシン-4-オン誘導体の合成とその有機合成への利用
• Cycloadditions in Syntheses. LII. Stereochemical Pathways of 1-Isoquinolone-Chloroehylene Photo[2+2]cycloaddition : Determination of Regio- and Stereostructures of the Products and Explanation for Their Formation
• FACILE SYNTHESIS OF THE CARBOCYCLIC ANALOGUE OF β-RIBOFURANOSYL-MALONATE, NEW SYNTHON FOR CARBOCYCLIC C-NUCLEOSIDE FORMATION BY RETROGRADE ALDOL C-C BOND FISSION
• 光化学的周辺環状反応を用いる生理活性化合物の合成
• Reaction of 2,2-Dimethyl-1,3-dioxin-4-one Derivatives with Pyridinium (Isoquinolinium) Methylides and Cyano Compounds

もっと見る 閉じる

スポンサーリンク