Synthetic Application of Benzothiazole Ring System as an On-Off Type of Leaving Group. Synthesis of Ketones and Carboxylic Acid Derivatives from 2-(1-Substituted 1-Hydroxyalkyl)- and 2-(1-Hydroxyalkyl)benzothiazoles.
スポンサーリンク
概要
- 論文の詳細を見る
A synthetic and systematic use of benzothiazole ring system as an "on-off" type of leaving group was developed for the preparation of ketones and carboxylic acid derivatives from a variety of 2-(1-substituted 1-hydroxyalkyl)- and 2-(1-hydroxyalkyl)benzothiazoles (off state) via the corresponding benzothiazolium salts (on state) obtained by the quaternization (on switch). A variety of 3-methyl-2-(1-substituted 1-hydroxyalkyl)benzothiazolium iodides (<B>1</B>) underwent a carbon–carbon bond cleavage at the 2-position to give the corresponding ketones on the simple treatment with a base under mild reaction conditions. The similar reaction of 3-methyl-2-(1-hydroxy-alkyl)benzothiazolium iodides (<B>2</B>) to aldehydes proceeded less efficiently. The oxidative reaction of a variety of <B>2</B> with base and nonactivated MnO<SUB>2</SUB> in ethanol afforded the corresponding ethyl esters. This type of oxidative reaction could be also achieved in THF with different nucleophiles such as alcohol, water, thiol, and amine to give the corresponding ester, carboxylic acid, thioester, and amide, respectively.
- 公益社団法人 日本化学会の論文
著者
-
Chikashita Hidenori
Department Of Applied Chemistry Faculty Of Engineering Kansai University
-
Itoh Kazuyoshi
Department Of Applied Chemistry Faculty Of Engineering & High Technology Research Center Kansai
-
Ishihara Masayuki
Department of Applied Chemistry, Faculty of Engineering, Kansai University
-
Takigawa Katsumi
Department of Applied Chemistry, Faculty of Engineering, Kansai University
関連論文
- Transient Thermoelastic Problem for a Laminated Composite Hollow Sphere with an Interlayer of Functionally Graded Material
- Exact Solution of Transient Thermal Stress Problem of a Multilayered Magneto-Electro-Thermoelastic Hollow Cylinder
- Direct Welding between Copper and Glass Substrates with Femtosecond Laser Pulses
- Multi-Spectral Two-Photon Excited Fluorescence Microscopy Using Supercontinuum Light Source
- The Cyclodehydration Route to the Asymmetric Total Synthesis of the Marine Natural Product Isolated from the Brown Alga, Notheia Anomala
- Highly Diastereoselective Addition of Methyllithium to Chiral α,β-Dialkoxy Ketones and Its Application to the Stereocontrolled Asymmetric Synthesis of Highly Substituted Tetrahydrofurans
- Generalization of Shift Invariant Neural Networks : Image Processing of Corneal Endothelium
- Learning Generalization by Validation Set
- Detection of Cell Membranes in Human Corneal Endothelial Micrograms Using Mathematical Morphology
- Optical Time-to-Three-Dimensional (3-D) Space Interconversion System
- Stereochemical Studies of Chiral Nonconjugated Carbanions. Asymmetric Alkylation of Aldehydes with Sulfur-Substituted Carbanions of Chiral α-(1,3-Dithian-2-yl) Acetals
- Bipolar Morphology and Its Applications (OPTICAL COMPUTING 1)
- Optoelectronic Implementation of Bipolar Analog Neural Network Using Shadow Casting (OPTICAL COMPUTING 1)
- Welding of Transparent Materials Using Femtosecond Laser Pulses
- Estimation of the Refractive Index Change in Glass Induced by Femtosecond Laser Pulses
- Dispersive Coherence Spectrotomography with White-Light Continuum
- Coherent Array of White-Light Continuum Generated by Microlens Array
- Coherence Spectrotomography of Layered Medium with White-Light Continuum
- Invariant Pattern Recognition Using Neural Networks Combined with Optical Wavelet Preprocessor
- Real-time Optical Wavelet-Transform with Positive and Negative Signals
- Plasma Cell Granuloma Extending from the Extracranial to the Intracranial Space Associated with Epstein-Barr Virus Infection : Case Report
- Interaction between Two Piezoelectric Inhomogeneities and a Crack in an Infinite Body(Fracture Mechanics)
- An Electroelastic Problem of an Infinite Piezoelectric Body with Two Inhomogeneities
- Depth-Resolved Observation of Photoelastic Effect by Four-Wave Mixing Microscopy
- Three-Dimensional Profiling of Refractive Index Distribution inside Transparent Materials by Use of Nonresonant Four-Wave Mixing Microscopy
- Proposal of Micro-Trichroic Structures for High-Sensitivity Color Image Sensors
- Realization of a Gravity-Capillary Wave Surface Using Sub-Nyquist Spectral Samples
- Optical Learning Neural Network Using Photorefractive Waveguides
- A Novel Spread Function for Observation of Random Surface
- Modification of Photorefractive Waveguides in Lithium Niobate by Guided Beam for Optical Dynamic Interconnection
- Application of Multiple-Image Fourier Transform Spectral Imaging to Measurement of Fast Phenomena
- Dual-Band Stimulated Parametric Emission Microscopy
- Three-Dimensional Unstained Live-Cell Imaging Using Stimulated Parametric Emission Microscopy
- Nonlinear Phase Imaging Using Two-Beam Interferometry in Stimulated Parametric Emission Microscopy
- Compact Spectral Imaging System Using Liquid Crystal for Fast Measurement
- Analysis of Photo-Induced Waveguide in Lithium Niobate Crystal
- Three-Dimensional Waveguides Fabricated in Poly(methyl methacrylate) by a Femtosecond Laser
- Generation of Debris in Water-Assisted Femtosecond Laser Drilling of Silica Glass
- Fabrication of Dammann Gratings in Silica Glass Using a Filament of Femtosecond Laser
- Characterization of Micro-Channels Fabricated by In-Water Ablation of Femtosecond Laser Pulses
- Volume Grating Induced by a Self-Trapped Long Filament of Femtosecond Laser Pulses in Silica Glass
- Stereocontrolled 1,4-Asymmetric Reduction of Cyclic Hemiketals. Synthesis of Both anti-and syn-1,4-Diols, and Their Transformations into trans-and cis-2,5-Disubstituted Tetrahydrofurans
- Stereoselective Synthesis of trans-2, 5-Disubstituted Tetrahydrofurans via the Lewis Acid Mediated Reduction of Cyclic Hemiketals with Triphenylsilane
- Activation of Sn-Se Bond:Regioselective Ring Opening Reaction of Epoxides with Tributylstannyl Phenylselenolate in the Presence of a Lewis Acid
- Interferometric Spectral Imaging and Optical Three-Dimensional Fourier Transformation
- A New Stereocontrolled Route to trans-2, 5-Disubstituted Tetrahydrofurans
- Coherence Spectrotomography : Optical Spectroscopic Tomography with Low-Coherence Interferometry
- An Operator Method of the Theory of Optical Coherence and Radiometry
- An Electroelastic Problem of Two Interface Cracks between Matrix and Inhomogeneity Subjected to Anti-Plane Shear Stress and In-Plane Electric Displacement(Fracture Mechanics)
- Analysis and Compensation for Artifacts in Three-Dimensional Refractive Index Profiling by Four-Wave Mixing Microscopy
- Subharmonic Synchronization of Picosecond Yb Fiber Laser to Picosecond Ti:Sapphire Laser for Stimulated Raman Scattering Microscopy
- In situ Micro-Raman Investigation of Spatio-Temporal Evolution of Heat in Ultrafast Laser Microprocessing of Glass
- Serum levels of soluble secreted α-Klotho are decreased in the early stages of chronic kidney disease, making it a probable novel biomarker for early diagnosis
- Facile construction of optically active 1,3-diols. Synthesis of (2S,4R)-7-octene-2,4-diol and endo-(1S,3S,5R)- and exo-(1R,3S,5S)-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.
- Highly Sensitive Signal Detection in Stimulated Parametric Emission Microscopy Based on Two-Beam Interferometry
- Synthetic Application of Benzothiazole Ring System as an On-Off Type of Leaving Group. Synthesis of Ketones and Carboxylic Acid Derivatives from 2-(1-Substituted 1-Hydroxyalkyl)- and 2-(1-Hydroxyalkyl)benzothiazoles.
- Lewis acid-promoted cross aldol reaction of aldehydes with ketones utilizing 3-methyl-2-phenyl-2-(2-oxoalkyl)benzothiazolines as an enolate-transferring reagent.
- Multi-Spectral Two-Photon Excited Fluorescence Microscopy Using Supercontinuum Light Source
- Stereoselective syn-reduction of (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes with metal hydride reagents.
- Nonacidic and highly chemoselective protection of the carbonyl function. 3-Methylbenzothiazolines as a base- and acid-resistant protected form for the carbonyl groups.
- In situ generation and synthetic application of 2-phenylbenzimidazoline to the selective reduction of carbon-carbon double bonds of electron-deficient olefins.
- Synthesis of 2[1-(alkoxycarbonyl)alkyl]-3-methylbenzothiazolines and 3-methyl-2-(2-oxoalkyl)benzothiazolines by the direct alkylation of lithium enolates with 3-methylbenzothiazolium salts.
- General reactivity of 2-lithiobenzothiazole to various electrophiles and the use as a formyl anion equivalent in the synthesis of .ALPHA.-hydroxy carbonyl compounds.