Fluorinated Pyrido[2,3-c]pyridazines. I. Reductive Cyclization of Ethyl 2-Diazo-2-(5-fluoro-2-halonicotinoyl)acetate with Trialkylphosphine
スポンサーリンク
概要
- 論文の詳細を見る
A new and convenient synthesis of 6-fluoro-4(1H)-oxopyrido[2,3-c]pyridazine-3-carboxylate derizatives was achieved. One-pot reactions of ethyl 2-diazo-2-(6-chloro- and 6-tolylthio-5-fluoro-2-halonicotinoyl)acetates (9a and 9b, c) with tri-n-butylphosphine or tricyclohexylphosphine gave ethyl 7-chloro- and 7-tolylthio-6-fluoro-4(1H)-oxopyrido[2,3-c]pyridazine-3-carboxylates (12a and 12b), respectively. The reaction of 9a-c with triphenylphosphine gave {[1-ethoxycarbonyl-1-(6-chloro- and 6-tolylthio-5-fluoro-2-halonicotinoyl)methylene]hydrazono}triphenylphosphoranes (10a-c, R=Ph), which were hydrolyzed to the corresponding hydrazones 11a-c. Intramolecular cyclization of the hydrazones 11b and 11c furnished an alternative and efficient synthesis of 12b. Possible mechanisms for the reaction of 9 leading to 12 are discussed.
- 公益社団法人日本薬学会の論文
- 1990-12-25
著者
-
松本 純一
Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.
-
松本 純一
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
-
宮本 皓之
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.
-
宮本 皓之
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
関連論文
- Synthesis and Structure-Activity Relationships of 4-Amino-5-chloro-2-ethoxybenzamides with Six- and Seven-Membered Heteroalicycles as Potential Gastroprokinetic Agents
- Synthesis and Biological Activities of the Optical Isomers of (±)-4-Amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide (Mosapride)
- Novel Benzamides as Selective and Potent Gastrokinetic Agents. III. Synthesis and Structure-Activity Relationships of 4-amino-5-chloro-2-methoxy- and 2-Ethoxy-N-[(4-substituted 2-morpholinyl)methyl]-benzamides
- Synthesis of 7-Thio-substituted 4-Oxoquinoline-3-carboxylic Acids with Antibacterial Activity
- Novel Benzamides as Selective and Potent Gastrokinetic Agents. IV. Synthesis and Structure-Activity Relationships of 2-Substituted 4-Amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chlorobenzamides
- Ampicillin及びAmoxicillin誘導体の研究(第2報)Sodium 6-[D-2-(2-(4-Formyl-1-piperazinyl)-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxamido)-p-hydroxyphenylacetamido]penicillanate(PL-385)の分解物の構造
- Ampicillin及びAmoxicillin誘導体の研究(第3報)6-[2-[(Pyrido[2,3-d]pyrimidin-6-yl)methylamino]-2-phenylacetamido]penicillanic Acid誘導体, 6-[2-(4-Pyrimidinylamino)-2-phenylacetamido]penicillanic Acid誘導体及び-cephalosporanic Acid誘導体の合成
- Ampicillin及びAmoxicillin誘導体の研究(第1報)N-(Pyrido[2,3-d]pyrimidine-6-carbonyl)ampicillin及び-amoxicillin誘導体の合成と抗菌活性
- Pyridonecarboxylic Acids as Antibacterial Agents. V. Synthesis of 1-Vinyl-1,4-dihydro-4-oxo-1,8- and 1,6-naphthyridine-3-carboxylic Acids
- Pyridone-carboxylic Acids as Antibacterial Agents. I. Synthesis and Antibacterial Activity of 1-Alkyl-1,4-dihydro-4-oxo-1,8-and 1,6-naphthyridine-3-carboxylic Acids
- Imidazo- and Triazoloquinolones as Antibacterial Agents. Synthesis and Structure-Activity Relationships
- Synthesis and Biological Activity of 11-[4-(Cinnamyl)-1-piperazinyl]-6,11-dihydrodibenz[b, e]oxepin Derivatives, Potential Agents for the Treatment of Cerebrovascular Disorders
- Pyrido [2,3-d] pyrimidine Antibacterial Agents. IV. Synthesis of Metabolites of Piromidic Acid
- Syntheses of Pyrimido [4,5-c] pyridazine Derivatives. II. A Novel Reaction of α-Diazo-β-oxo-5-(4-chloropyrimidine) propionate with Triphenyl Phosphine leading to 1,4-Dihydro-4-oxopyrimido-[4,5-c] pyridazine-3-carboxylate
- Syntheses of Pyrimido [4,5-c] pyridazine Derivatives. I. A Novel Reaction of α-Diazo-β-oxo-5-(4-chloropyrimidine) propionate with Hydrazine leading to 1,2-Dihydro-4-hydroxypyrimido [4,5-c] pyridazine-3-carboxamide
- ピリド[2,3-d]ピリミジン系抗菌剤(第5報)1H, 5H-Imidazo[1,2-a]-pyrido[2,3-d]pyrimidine類の合成と反応
- Synthesis and Covalent Hydration of 4H-Pyrimido [1,6-α] pyrimidines
- ニトロフラン誘導体の研究(第9報)5-Nitro-2-furoyl Isothiocyanateおよび5-Nitro-2-thiofuroyl Isocyanateとβ-アミノクロトン酸エステル類との反応
- Pyrido [2,3-d] pyrimidine Antibacterial Agents. I. 8-Alkyl-5,8-dihydro-5-oxopyrido [2,3-d]-pyrimidine-6-carboxylic Acids and Related Compounds
- Pyrido [2,3-d] pyrimidine Antibacterial Agents. II. Piromidic Acid and Related Compounds
- Studies on Nitrofuran Derivatives. VIII. Synthesis of 3-(5-Nitro-2-furyl) isoxazoles.
- 1,3-Dipolar Cycloaddition of 5-Nitro-2-furonitrile Oxide
- Stidies on Nitrofuran Derivatives. III. Novel Self-condensations of 5-Nitro-2-furaldehyde and 5-Nitro-2-thenaldehyde
- Sythesis and Stereochemistry of 11-Amino-6,6a, 7,8,9,10,10a, 11-octahydrodibenzo[b, e]thiepines and-oxepines
- Fluorinated Pyrido[2,3-c]pyridazines. II. Synthesis and antibacterial Activity of 1,7-Disubstituted 6-Fluoro-4(1H)-Oxopyrido[2,3-c]pyridazine-3-carboxylic Acids
- Fluorinated Pyrido[2,3-c]pyridazines. I. Reductive Cyclization of Ethyl 2-Diazo-2-(5-fluoro-2-halonicotinoyl)acetate with Trialkylphosphine
- Regioselective Displacement Reactions of 1-Cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylic Acid with Amine Nucleophiles
- An Improved Optical Resolution of 3-Acetylthio-2-methylpropionic Acid by Use of a New Chiral Amine, N-Isopropyl(phenylalaninol)
- Synthesis and Antiallergic Activity of N-[4-(4-Diphenylmethyl-1-piperazinyl)butyl]-1,4-dihydro-4-oxopyridine-3-carboxamides
- Synthesis and Antiucler Activity of the Metabolites of 2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline Dimaleate(AS-2646), a Novel Gastric Antisecretory and Antiulcer Agent
- A Novel Class of Antiulcer Agents. 4-Phenyl-2-(1-piperazinyl)quinolines
- Fluorocinnoline Derivatives. II. : Synthesis and Antibacterial Activity of Fluorinated 1-Alkyl-1,4-dihydro-4-oxocinnoline-3-carboxylic Acids
- A New Cinnoline Ring Construction by the Reaction of 2-Diazo-3-(2-fluorophenyl)-3-oxopropionates with Tri-n-buthylphosphine
- Pyridonecarboxylic Acids as Antibacterial Agents. XII. : Synthesis and Antibacterial Activitity of Enoxacin Analogues with A Variant at Position 1
- Pyridonecarboxylic Acids as Antibacterial Agents. VIII. An Alternative Synthesis of Enoxacin via Fhioronicotinic Acid Derivatives(Organic,Chemical)
- A New Synthesis of 7H-Pyrido[1,2,3-de][1,4]benzoxazine Derivatives Including an Antibacterial Agent, Ofloxacin