Syntheses and reactions of enamines from 9-formylfluorene

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概要

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• Many enamines 3 from 9-formylfluorene (1) were easily prepared by the reaction of 1 with several aliphatic, aromatic, alicyclic and heterocyclic secondary amines 2 in aqueous ethanol at room temperature. The reaction of 9-morpholinomethylenefluorene (3i), a typical 3, with bromine in dichloroethane gave the corresponding iminium bromide (4). The hydrolysis of 4 with water afforded 9 -bromo- 9 -formylfluorene (6). 2,2-Biphenylene-1, 1-dialkoxyethylene 10 was obtained from 9 -bromo- 9 -formylfluorene dialkyl acetal which was derived from 6 with alkyl orthoformate in alcohols under acidic conditions. Compound 10 was also obtained from 4 via 2, 2-biphenylene-1, 1-dialkoxy- 1 -morpholinoethane. Furthermore, the reactions of 3i with ethyl azidoformate and with P-toluenesulfonyl azide were investigated.

• 山口大学の論文

著者

• Nishida A

  Yamaguchi Univ.

• NISHIDA Akiko

  Department of Applied Chemistry and Chemical Engineering

• FUJISAKI Shizuo

  Department of Applied Chemistry and Chemical Engineering

• KAJIGAESHI Shoji

  Department of Industrial Chemistry

• KADAYA Naoyuki

  Idemitsu Kousan, Central Research Laboratory

• Kajigaeshi Shoji

  Department Of Applied Chemistry And Chemical Engineering Faculty Of Engineering Yamaguchi University

• Fujisaki S

  Department Of Applied Chemistry And Chemical Engineering

• Fujisaki Shizuo

  Department Industrial Chemistry

• Nishida Akiko

  Department Of Anesthesiology Gunma University School Of Medicine

• Kadaya Naoyuki

  Idemitsu Kousan Central Research Laboratory

関連論文

• Rotational isomerisum in fluorene derivatives XXIII syntheses of 1-substituted 1'-methyl-9, 9'-bifluorenyl derivatives and their conformational isomerisum
• Rotational isomerism in fluorene derivatives XXII syntheses of 1-substituted 2'-methyl-9, 9'-bifluorenyl derivatives and structures of their stereoisomers
• Pyridine ring formation by the reaction of conjugated carbodiimides with enamines
• Synthesis of tropolone and tropone derivatives condensing fluorene moiety
• Synthesis and properties of 3-aminoacrylonitriles
• Oxidation using quaternary ammonium polyhalides VII. Oxidation of primary amines and hydrazo compounds by use of benzyltrimethylammonium tribromide
• Halogenation using quaternary ammonium polyhalides XXVIII. effect of substituents on brominating ability of quaternary ammonium tribromides
• Syntheses and reactions of enamines from 9-formylfluorene
• Rotational Isomerism in Fluorene Derivatives XIV Conformational Equilibria of 9-Substituted 9-(2-Cyanomethylphenyl) fluorene Derivatives
• Synthesis of 2-dialkylamino-5-hydroxy-1, 3-dithian-2-ylium perchlorates and their intramolecular rearrargements by use of bases
• Deuteration of Bromophenol Derivatives with Cu-Al Alloy in a D_2O Solution of Sodium Carbonate or Barium Oxide
• The Effects of Various GTP Analogues on Microtubule Assembly
• Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide
• Selective Bromination of Aromatic Amines by Use of Tetrabutylammonicm Tribromide and Benzyltrimethlammonnium Tribromide
• Halogenation Using Quaternary Ammonium Polyhalides XX V : Bromination of Acetanilides with Benzytrimethylammonium Tri-bromide-Zinc Chloride System
• Halogenation Using Quaternary Ammonium Polyhalides XX II : Selective Bromination of Aromatic Ethers with Benzyltrimeth-ylammouium Tribromide
• Halogenation Using Quaternary Ammonium Polyhalides XX IV : Chlorination of Acetanilides with Benzyltrimethylam-monium Tetrachloroiodate
• Halogenation Using Quaternary Ammonium Polyhalides XX VI : CHLORINATION OF PHENOLS WITH BEN-ZYLTRIMETHYLAMMONIUM TETRACHLOR-OIDATE
• Halogenation Using Quaternary Ammonium Polyhalides XX III : Bromination of Aromatic Amines with Polymer-bound Benzytrimethylammonium Tribromide
• Halpgenation Using Quaternary Ammonium Polyhalides XXI : Chlorination of Some Aromatic Compounds with Tetrabutylammonium Trichloride
• Oxidation Using Quaternary Ammonium Polyhalides V : Selective Oxidation of Benzyl Alcohols by the Use of Benzyltyimethylammonium Tribromide
• Oxidation Using Quaternary Ammonium Polyhalides IV ; Selective Oxidation of Sulfides to Sulfoxides with Benzyltrimethylammonium Tribromide
• Halogenation Using Quaternary Ammonium Polyhalides XX : Bromination of Phenols Polymer-Bound Benzyltrimethylammouium Tri-bromide
• Facile Synthesis of N-Bromoamides Using Benzyltrimethylammonium Tribromide in Alkaline Solution
• Halogenation Using Quaternary Ammonium Polyhalides X IX. Aromatic Chlorination of Arenes with Benzyltrimethylammonium tetrachloroiodate
• Halogenation Using Quaternary Ammoniun Polyhalides X VII. lodination of Acetanilide Derivatives with benzyltrimethylammonium dichloroiodate and ZnC12
• An Efficient Method for the Hofmann Degradation of Amides by Use of Benzyltrimethylammonium Tribromide
• Facile Synthesis of Chloro-substituted Aromatic Ethers by Use of Benzyltrimethylammonium Tetrachloroiodate
• ACONVENIENT HALOFORM REACTION USING BENZYLTRIMETHYL AMMONIUM TRIBROMIDE
• Bromination of Alkenes and Related Compounds by Use of Benzyltrimethylammonium Tribromide in Aprotic and Protoc Solvents
• Bromination of Alkenes and Related Compounds by Use of Benzyltrimethylammonium Tribromide in Aprotic and Protic Solvents
• Halogenation Using Quaternary Ammonium Polyhalides. V. lodination of Phenols by Use of Benzyltrimethylammonium Dichloro iodate (1-)
• Halogenation Using Quaternary Ammonium Polyhalides X IV. Aromatic Bromination and lodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
• Bromination of Aromatic Amines by Use of benzyltrimethylammonium chlotomate (1-)
• α-CHLORINATION OF ACETOPHENONE DERIVATIVES BY USE OFBENZYLTRIMETHYL-AMMONIUM TETRACHLOROIODATE
• Facile Synthesis of Bromosubstituted Aromatic Ethers by Use of Tetraalkylammonium Polyhalides
• Halogenation Using Quaternary Ammonium Polyhalides. XII. lodination of Aromatic Ethers by Use of Benzyltrimethylammonium Dichloroiodate and zine chloride
• Halogenation Using Quaternary Ammonium Polyhalides. XI. Bromination of Acetanilides by Use of Tetraalkylammonium Polyhalides
• Halogenation Using Quaternary Ammonium Polyhalides. VIII. Bromination of Phenols by Use of Benzyltrimethylammonium Chlorobromate (1-)
• Halogenation Using Quaternary Ammonium Polyhalides. VII. lodination of Aromatic Amines by Use of Benzyltrimethylammonium Dichloroiodate (1-)
• Halogenation Using Quaternary Ammonium Polyhalides. IV. Selective Bromination of Phenols by Use of Tetraalkylammonium Tribromides
• ANEFFECTIVE CHLORINATING AGENT BENZYLTRIMETHYLAMMONIUM TETRACHLOROIODATE, BENZYLIC CHLORINATION OF ALKYLAROMATIC COMPOUNDS
• Chlorination of some aromatic compounds with tetrabutylammonium trichloride
• Benzylic Bromination of Arenes by Use of Benzyltrimethylammonium Tribromide
• Halogenation Using Quaternary Ammonium Polyhalides. X. α-Chlorination of Aromatic Acetyl Derivatives with Benzyltrimethylammonium Dichloroiodate
• Bromination of aromatic amines by use of benzyltrimethylammonium chlorobromate (1-)
• Practical synthesis of N-bomoamides with benzyltrimethylammonium tribromide in the presence of aqueous disodium hydrogenphosphate
• Bromination of phenols by use of benzyltrimethylammonium chlorobromate (1-)
• Use of rocuronium-sugammadex, an alternative to succinylcholine, as a muscle relaxant during electroconvulsive therapy
• 1, 3-dipolar addition of nitrile oxides to 3a, 4-dihydro-1-isoindolinones
• Comparison of recovery times from rocuronium-induced muscle relaxation after reversal with three different doses of sugammadex and succinylcholine during electroconvulsive therapy
• Studies on Fluorene Derivatives. XIII. The Formation of Tribiphenylenepropane by Self-condensation of Dibiphenyleneethylene
• Synthesis and properties of 4H-benzo[hi]pyrrolo[2,1,5-cd]indolizin-4-ones.
• exo-Selective peripheral cycloaddition reactions of pyrido(2,1-a)isoindole.
• Halogenation using quaternary ammonium polyhalides. XXIV. Chlorination of acetanilides with benzyltrimethylammonium tetrachloroiodate.
• Halogenation using quaternary ammonium polyhalides. XIX. Aromatic chlorination of arenes with benzyl-trimethylammonium tetrachloroiodate.
• Rotational isomerism in fluorene derivatives. XVI. Conformational equilibria of 9-substituted 9-(2'-bromomethylphenyl)fluorene derivatives.
• Rotational isomerism in fluorene derivatives. III. The conformation of 9-(9-fluorenyl)-9-(2-substituted 9-fluorenyl)fluorene derivatives.
• Oxidation using quaternary ammonium polyhalides. IV. Selective oxidation of sulfides to sulfoxides with benzyltrimethylammonium tribromide.
• Halogenation using quaternary ammonium polyhalides. IV. Selective bromination of phenols by use of tetraalkylammonium tribromides.
• Synthesis of dibromoacetyl derivatives by use of benzyltrimethylammonium tribromide.
• Halogenation using quaternary ammonium polyhalides. XVII. Iodination of acetanilide derivatives with benzyltrimethylammonium dichloroiodate and zinc chloride.
• Halogenation using quaternary ammonium polyhalides. xi. Bromination of acetanilides by use of tetraalkylammonium polyhalides.
• Halogenation Using Quaternary Ammonium Polyhalides. XXXI. Halogenation of Thiophene Derivatives with Benzyltrimethylammonium Polyhalides.
• Oxidation using quaternary ammonium polyhalides. VIII. Oxidation of 1,4-benzenediols with benzyltrimethylammonium tribromide.
• Studies on fused pyrimidine derivatives. Part IX. Thermal reactions of 6-methyl-5-((substituted hydrazono)methyl)-2,4(1H,3H)-pyrimidinediones with electron-deficient olefins and acetyle ne.
• Preparation of pyrido- and azepino-fused cycl(3.2.2)azines.
• Rotational isomerism in fluorene derivatives. X. The conformational equilibria of 9-substituted 9-(2-methylthiophenyl)- and 9-substituted 9-(2-methylsulfinylphenyl)fluorene derivatives.
• Halogenation using quaternary ammonium polyhalides. VI. Bromination of aromatic amines by use of benzyltrimethylammonium tribromide.
• Regio- and stereoselective introduction of functional groups into 1-isoindolinone and 1(2H)-isoquinolone systems.
• A kinetic study on reduction of 9,9'-bifluorenylidene by sodium isopropoxide.
• Halogenation using quaternary ammonium polyhalides. IX. One-step syntheses of acylureas and carbamates from amides by use of tetrabutylammonium tribromide and DBU.
• A facile one-pot synthesis of sulfides from alkyl halides and alcohols using tetramethylthiourea.
• Selective preparation of fluorene derivatives using the t-butyl function as a positional protective group.
• Rotational isomerism in fluorene derivatives. XV. Conformational equilibria of 2-substituted and 2,7-disubstituted 9-(2'-dimethylaminophenyl)fluorene derivatives and the effects of acid on them.
• A practical synthesis of N-bromo imides by use of sodium bromite.
• Rotational isomerism in fluorene derivatives. IX. Restricted rotation about the C(9)-C(9') bonds in 9(or 9')-substituted 2-methyl-9,9'-bifluorenyls.
• Studies on fused pyrimidine derivatives. Part VIII. The characterization and cycloaddition reaction of 5,6-dihydro-1,3-dimethyl-6-methylene-5-((substituted amino)methylene)-2,4(1H, 3H)-pyrimidinediones.
• Oxidation using quaternary ammonium polyhalides. III. An effective oxidation of alcohols and ethers by the use of benzyltrimethylammonium tribromide.
• Halogenation using quaternary ammonium polyhalides. XXVII. Chloroiodination of alkenes with benzyltrimethylammonium dichloroiodate.
• Syntheses and Ring Opening Reactions of 2-Alkyl-3,3-dichlorospiro-[cyclopropane-1,9′-fluorene] Derivativatives
• Oxidation using quaternary ammonium polyhalides. V. Selective oxidation of benzyl alcohols by the use of benzyltrimethylammonium tribromide.
• Azafulvenes. 8. Cycloaddition reaction of 8-azaheptafulvene to sulfene.

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