A Synthesis of Heteroaromatic Analogues of 1-Methyl-1,2,3,4-tetrahydroisoquinoline Using the Pummerer-Type Cyclization Reaction : Observation of Tandem Cyclization Reaction
スポンサーリンク
概要
- 論文の詳細を見る
The sulfoxides 7b and 7d carrying thiophene or benzothiophene as heteroaromatic nucleophiles, when treated with trifluoroacetic anhydride at room temperature (Pummerer reaction), underwent an intramolecular alkylation in an exclusive manner to yield 4,5,6,7-tetrahydro-7-methyl-4-phenylsulfanylthieno[2,3-c]pyrtdine-6-carbaldehyde (10) and the corresponding benzothiophene derivative (12b) in high yields, respectively. Thus, this route provides biologically interesting nitrogen heterocycles (1b) and (2b). On the other hand, the sulfoxide (7c) carrying benzofuran as a nucleophile on reaction with TFAA yielded not only the Pummerer-type cyclization product (12a), but also the diastereoisomeric tandem cyclization products (13) and (14) having a noble 11-aza-2-oxa-7-thiatricyclo[4.3.3.0^<1.5>]dodecane ring system (B). The formation of these products can be readily rationalized by the intervention of the oxonium ion intermediate (21).
- 公益社団法人日本薬学会の論文
- 2004-02-01
著者
-
佐野 武弘
昭和薬科大学
-
佐野 武弘
Showa Pharmaceutical Univ. Tokyo Jpn
-
SANO Takehiro
Showa College of Pharmaceutical Sciences
-
SAITOH Toshiaki
Showa College of Pharmaceutical Sciences
-
HORIGUCHI Yoshie
Showa College of Pharmaceutical Sciences
-
Ogawa K
Showa Pharmaceutical University
-
OGAWA Keita
Showa Pharmaceutical University
-
Horiguchi Y
Showa Pharmaceutical University
関連論文
- Purines. LXX. An Extension of the "Phenacylamine Route" to the Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine, and Antileukemic Activity of Some Purine N-Oxides
- Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
- Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
- Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
- Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
- Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
- Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
- 90(P04) β-エリスロイジンの合成研究(ポスター発表の部)
- ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE : CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
- REARRANGEMENT OF 2,3-DIOXO-1,4-OXAZINES TO 4,5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE
- Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure
- Synthesis of Highly Deydrogenated Oxoerythrinan Alkaloids, Erytharbine and Crystamidine
- Dioxypyrrolines. LV. Stereochemical Pathway of [2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Cycloalkadienes and Cycloalkenes
- Dioxopyrroline. LIV. Steretchemical Pathway of[2+2]Photocycloaddition Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione to Acyclic Olefins
- Dioxopyrrolines. LIII.Stereochemical Pathway of [2+2] Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Cyclic Enol Trimethylsilyl Ethers
- Synthesis and Reactions of 3,7-Cycloerythrinan : Skeletal Rearrangement of 2,7,8-Trioxoerythrinans to 4-Oxo-4H-pyrido[2,1,-a]isoquinolines
- Synthesis of Erythrina and Related Alkaloids.XXIV. Total Synthesis of Erysotrine from 1,7-Cycloerythrinan Derivatives by the Use of a New 1,2-Carbonyl Transposition Method
- Synthesis of Erythrina and Related Alkaloids. XXIII. : Intramolecular Cyclization Approach. (2). Synthesis and Reactions of 1,7-Cyclo-cis-erythrinans, Potential Intermediates to Natural Erythrina Alkaloids
- Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone
- Studies toward Total Synthesis of Non-aromatic Erythring Alkaloids. (6). Synthesis of 8-OXO-γ-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
- Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (4). Oxidation of Furan Ring of D-Furanoerythrinans with N-Bromoacetamide
- Dioxopyrrolines. XLIII. : Diels-Alder Reaction of 4,5-Diethoxycarbonyl-1H-pyrrole-2,3-dione with Butadienes : Synthesis of Polyfunctionalized Hydroindoles
- Two New Morphinane Alkaloids from Stephania cepharantha HAYATA (Menispermanceae)
- Synthesis of Erythrina and Related Alkaloids. XXX. Photochemical Approach. (1). Synthesis of Key Intermediates to Erythrina Alkaloids by Intermolecular [2+2] Photocycloaddition Followed by 1,3-Shift
- Dioxopyrroline. L. Skeletal Rearrangements of 7-Vinyl-7-trimethylsilyloxy-5-ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones under Thermal, Basic, and Acidic Conditions
- Dioxopyrrolines. XLVII. : Thermal Rearrangements of 7-Vinyl Derivatives of 1-Aryl-5-ethoxy-carbonyl-2-azabicyclo[3.2.0]heptane-3,4-diones and Their Imidates
- Synthesis of Erythrina and Related Alkaloids. XVI. Diels-Alder Approach: Total Synthesis of dl-Erysotrine, dl-Erythraline, dl-Erysotramidine, dl-8-Oxoerythraline and Their 3-Epimers(Organic,Chemical)
- 26 ホモエリスリナアルカロイド,(±)schelhammericine,(±)3-epischelhammericineの全合成
- TOTAL SYNTHESIS OF THE HOMOERYTHRINAN ALKALOIDS, SCHELHAMMERICINE AND 3-EPISCHELHAMMERICINE
- Dioxopyrrolines. XLIV. : Thermal 1,3-Shift of 2-Azabicyclo[3.2.0]hept-2-ene Ring System : A New Entry to 3,4-Dihydropyridines and 2-Azanorborn-2-enes
- Dioxopyrrolines.XLII. : Mechanism of 7-Epimerization Reaction of 7-Substituted 5-Ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones
- Dioxopyrrolines. XXXV. Synthesis of 2H-Azepin-2-ones (2-Azatropones)
- Lycopodium植物トリテルペノイドの化学分類学的研究
- [2+2] Photocycloaddition Reaction of 5-Arylfuran-2,3-diones to Trimethylsilyloxyethylenes
- Dioxopyrrolines. LXI. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione with 1,3-Dienes : Competitive Occurrence of Normal and Hetero Diels-Alder Reaction and Claisen Rearrangement of the Hetero Diels-Alder Product
- Total Synthesis of Homoerythrinan Alkaloids, Schelhammericine and 3-Epischelhammericine
- Dioxopyrrolines. XLIX. Synthesis of Azatropolones via Photocycloaddition of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-diones to Acetylenes and Ethylenes
- Dioxopyrrolines. XLVIII. : Regioselective Formation of Hydroindoles via Photochemical and Thermal Cycloaddition Reactions of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-dione with Isoprene
- Dioxopyrrolines. XLVI. : [2+2] Photocycloaddition of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Six-Membered Cycloolefins : Effect of Ring Size on Stereochemical Pathways
- Dixopyrrolines. XLV. : [2+2] photocycloaddition of 4-Ethoxycarbonyl-5-aryl-1H-pyrrole-2,3-dione to Cyclopentene Derivatives : Formation of Dihydropyridones
- Dioxopyrrolines. XLI. : X-Ray Crystallographic Determination of the Stereochemistry of an Azatricyclo[5.3.0.0^]decane Derivative Obtained by Photocycloaddition of Cyclopentadiene to 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione
- Dioxopyrrolines. XL. Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Dihydrofurans. Formation of a 2,4-Dioxa-10-azatricyclo[6.3.0.0^]undecane Ring System(Organic,Chemical)
- Dioxopyrrolines. XXXVII. Stereochemical Pathways of Dioxopyrroline-Olefin Pbotocycloaddition. Stereochemical Selection Rule for the Photocycloaddition of Enone-Olefin Pairs(Organic,Chemical)
- Dioxopyrrolines. XXXVI. [2+2] photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Acyclic Olefins. Structural and Stereochemical Assignment of the Photocycloadducts(Organic,Chemical)
- Dioxopyrrolines. XXIX. Solvolytic Behavior of 3-Ethoxycarbonyl-2-phenyl-Δ^2-pyrroline-4,5-diones in Protic Solvents
- Alkaloidal Constituents of the Leaves of Stephania cepharantha Cultivated in Japan : Structure of Cephasugine, a New Morphinane Alkaloid
- Alkaloidal Constituents of the Tubers of Stephania cepharantha Cultivated in Japan : Structure of 3,4-Dehydrocycleanine, a New Bisbenzylisoquinoline Alkaloid
- A Synthesis of 3-Phenyl-1, 2, 3, 4-tetrahydroisoquinoline and 2-Phenyl-1, 2, 4, 5-tetrahydro-3H-3-benzazepine via Pummerer-Type Cyclization : Enhancing Effect of Boron Trifluoride Diethyl Etherate on the Cyclization
- A Synthesis of 2,3,4,5-Tetrahydro-1H-3-benzazepines via Pummerer-Type Cyclization of N-(2-Arylethyl)-N-(2-phenylsulfinylethyl)formamides
- A Synthesis of Chiral 1,1,3-Trisubstituted l,2,3,4-Tetrahydro-β-carbolines by the Pictet-Spengler Reaction of Tryptophan and Ketones: Conversion of (1R,3S)-Diastereomers into Their (1S,3S)-Counterparts by Scission of the C(1)-N(2) Bond
- A Convenient Synthesis of 1, 1-Disubstituted 1, 2, 3, 4-Tetrahydroisoquinolines via Pictet-Spengler Reaction Using Titanium(IV)Isopropoxide and Acetic-Formic Anhydride
- A Synthesis of Heteroaromatic Analogues of 1-Methyl-1,2,3,4-tetrahydroisoquinoline Using the Pummerer-Type Cyclization Reaction : Observation of Tandem Cyclization Reaction
- Super Acid-Induced Pummerer-Type Cyclization Reaction : Improvement in the Synthesis of Chiral 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinolines
- Intramolecular Capture of Pummerer Reaction Intermediates by an Aromatic Nucleophile : Selective Construction of 1, 4-Benzothiazine and Indole Ring Systems
- Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfinyl)propionamides
- A Chiral Synthesis of Four Stereoisomers of 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome
- [2+2] Photocycloaddition Reaction of 5-Phenyl-1H-furan-2,3-dione to Phenylethylene
- A Novel Synthesis of 1,2,3,4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N-[(phenylsulfinyl)propyl]formamide
- 脳内アミン,1-メチルテトラヒドロイソキノリンのパーキンソン病治療薬としての可能性
- A Synthesis of Mono- and Dimethoxy-1,2,3,4-tetrahydroisoquinolines via Pummerer Reaction : Effects of Methoxyl Groups on Intramolecular Cyclization
- General Method for Synthesis of Erythrinan and Homoerythrinan Alkaloids (1) : Synthesis of a Cycloerythrinan, as a Key Intermediate to Erythrina Alkaloids, by Pummerer-Type Reaction
- Determination of Ring Conformation in 1-Benzyl-1,2,3,4-tetrahydroisoquinolines and a New Synthesis of the Chiral Compounds
- An Improved Synthesis of 1,2,3,4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl)methyl-2-(phenylsulfinyl)ethylamine by Pummerer Reaction
- Synthesis of Homoerythrinan Alkaloids of 1(2)-Alkene and 1,6-Diene Types : Total Synthesis of Comosine, Dihydroschelhammeridine, Schelhammeridine, and 3-Epischelhammeridine
- A Synthesis of 1-Azaanthraquinones via Diels-Alder Reaction of 4-Hydroxy- and 4-Methoxy-2-phenylquinolinequinones with 3-Trimethylsilyloxy-1,3-butadienes : Observation of Inverse Regioselectivity
- Thermal Addition Reaction of Aroylketenes with Cyclic Enol Ethers
- Thermal Addition Reaction of Aroylketene with 1-Aryl-1-trimethylsilyloxyethylenes : Aromatic Substituent Effects of Aroylketene and Aryltrimethylsilyloxyethylene on Their Reactivity
- エリスリナおよび関連アルカロイドの合成
- Synthesis of 2,3,4,5-Tetrahydro-1H-2-benzazepines via Pummerer-Type Cyclization of N-Arylmethyl-N-(3-phenylsulfinylpropyl)formamides
- Dioxopyrrolines. LX. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione to Olefins : An Inverse-Electron-Demand Hetero Diels-Alder Reaction
- Alkaloidal Constituents of Vines of Stephania cepharantha(Natural Medicine Note)
- ジオキソピロリンを利用した種々の含窒素複素環化合物の合成