New Methods and Reagents in Organic Synthesis. 35. A New Synthesis of Some Non-Steroidal Anti-Inflammatory Agents with the 2-Arylpropionic Acid Skeleton by the Use of Diphenyl Phosphorazidate (DPPA) as a 1,3-Dipole

スポンサーリンク

概要

• 論文の詳細を見る

• Reaction of diphenylphosphinic azide (8) with the pyrrolidine enamine 13 of 4-isobutylpropiophenone afforded two amidines 15a and 16a, which were derived from the 1,3-dipolarcycloadduct 14a by the expulsion of nitrogen followed by 1,2-aryl migration (path a) and by 1,3-dipolar elimination (path b), respectively. Although diphenylthiophosphinic azide (9) and ethyl phenylthiophosphonoazidate (10) also gave similar results, diphenyl phosphorazidate (DPPA, (C_6H_5O)_2P(O)N_3) furnished the amidine 15d formed via path a as the sole isolable product. Hydrolysis of 15d with potassium hydroxide afforded ibuprofen (3) in good yield. Other nonsteroidal antiinflammatory agents, naproxen (4), ketoprofen (5), and flurbiprofen (6), were analogously and conveniently prepared from the ketones 17,22,and 25,respectively, by a similar three-step operation using pyrrolidine, DPPA, and potassium hydroxide. 2-(2-Dibenzofuranyl)-propionic acid (7) was also prepared from the ketone 28 by the three-step procedure.

• 1983-09-25

著者

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 加藤 信治

  Central Research Laboratories, Santen Pharmaceutical Co., Ltd.,

• 塩入 孝之

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 塩入 孝之

  名古屋市大・薬

• 河合 伸高

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 河合 伸高

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)central Research Laboratorie

• 加藤 信治

  Central Research Laboratories Santen Pharmaceutical Co. Ltd.

関連論文

• 82 海洋産抗腫瘍活性物質カリクリン類の合成研究(口頭発表の部)
• Total Synthesis of Avellanins A and B, New Fungal Metabolites from Hamigera avellanea with Pressor Effect
• On the Reaction of N, N'-Dimethylfumaranilide with Aluminium Chloride
• Syntheses of the Acridone Alkaloid Citrusinine-I and Its Derivatives
• New Methods and Reagents in Organic Synthesis. 43. A New Synthesis of tert-Butyl Peroxycarboxylates Using Diethyl Phosphorocyanidate (DEPC)
• New Methods and Reagents in Organic Synthesis. 15. Epoxidation of Olefins with Diethyl Phosphorocyanidate (DEPC) and Hydrogen Peroxide
• 9-4 鉄欠乏オオムギ根で誘導されるアルコールデヒドロゲナーゼ遺伝子について(9.植物の無機栄養)
• 16 鉄欠乏オオムギ根で発現するムギネ酸鉄トランスポーター遺伝子のスクリーニング法の検討(関東支部講演会)
• Amino Acids and Peptides. XXXI. Phosphorus in Organic Synthesis. XVIII. Synthesis of Porcine Motilin by the Solid-phase Method using Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC)
• Amino Acids and Peptides. XXX. Phosphorus in Organic Synthesis. XVII. Application of Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC) to Solid-phase Peptide Synthesis
• Amino Acids and Peptides. XXIX. A New Efficient Asymmetric Synthesis of α-Amino Acid Derivatives with Recycle of a Chiral Reagent-Asymmetric Alkylation of a Chiral Schiff Base from Glycine
• Molecular Conformation of Patellamide A, a Cytotoxic Cyclic Peptide from the Ascidian Lissoclinum patella, by X-Ray Crystal Analysis
• New Methods and Reagents in Organic Synthesis. 18. Homologation of Ketones with Trimethylsilyldiazomethane (TMSCHN_2)
• New Methods and Reagents in Organic Synthesis. 14. A Simple Efficient Preparation of Methyl Esters with Trimethylsilyldiazomethane (TMSCHN_2) and Its Application to Gas Chromatographic Analysis of Fatty Acids
• 36 海洋産抗腫瘍性環状ペプチドパテラマイド類の全合成
• REACTION OF TRIMETHYLSILYLDIAZOMETHANE WITH OLEFINS
• 15 Evans-Aldol反応を鍵工程とするドラスタチン10の立体選択的全合成(口頭発表の部)
• ムギネ酸生合成経路の研究 : ニコチアナミンアミノ基転移酵素の精製
• Amino Acids and Peptides. II. A One-Step Synthesis of Atropine and Other Related Alkaloids from dl-Phenylalanine 3α-Tropanyl Ester
• 8 PhenylalanineからTropic acidへの非酵素的転換反応
• Studies on Reaction Conditions and New Entry to Chiral Ligands in the Chiral Lithium Amide-Mediated Enantioselective Aldol Reaction
• Phosphorus in Organic Synthesis. XVI. Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC). Two New Reagents for the Preparation of Thiol Esters from Carboxylic Acids and Thiols
• Amino Acids and Peptides. XXVIII. A New Synthesis of α-Amino Acid Derivatives by Alkylation of Schiff Bases derived from Glycine and Alanine
• Amino Acids and Peptides. XXVII. A Novel Reductive Cleavage of N-C-N Bonds with Sodium Borohydride
• Amino Acids and Peptides. XXIV. Phosphorus in Organic Synthesis. XIII. Application of Diphenyl Phosphorazidate (DPPA) to the Synthesis of the Protected N-Terminal Hexapeptide of Secretin
• Phosphorus in Organic Synthesis. XII. Amino Acids and Peptides. XXII. Reaction of Penicillin Sulfoxides with Diethyl Phosphorocyanidate (DEPC)
• Phosphorus in Organic Synthesis. X. tert-Butyl Carbamate. An Efficient Additive in a Modified Curtius Reaction by Diphenyl Phosphorazidate (DPPA)
• Amino Acids and Peptides. XVIII. A Biogenetic-type, Asymmetric Synthesis of (S)-Reticuline from L-3-(3,4-Dihydroxyphenyl)-alanine by 1,3-Transfer of Asymmetry
• Amino Acids and Peptides. XVII. A Biogenetic-type, Asymmetric Synthesis of (S)-Laudanosine from L-3-(3,4-Dihydroxyphenyl) alanine by 1,3-Transfer of Asymmetry
• Amino Acids and Peptides. XVI. : A New Synthesis of α-Phenylglycine and Its Derivatives
• Amino Acids and Peptides. XV. : A New Synthesis of α-Amino Acids by Amination of α-Metalated Carboxylic Acids
• Amino Acids and Peptides. XIII. A New Approach to the Biogenetictype, Asymmetric Synthesis of Indole and Isoquinoline Alkaloids by 1,3-Transfer of Asymmetry
• Phosphorus in Organic Synthesis. IX. On the Mechanism of Esterification of Malonic Acid Half Esters by Diphenyl Phosphorazidate
• Amino Acids and Peptides. XII. Phosphorus in Organic Synthesis. VIII. Reaction of Malonic Acid Half Esters with Diphenyl Phosphorazidate
• Amino Acids and Peptides. XI. Phosphorus in Organic Synthesis. VI. Application of Diphenyl Phosphorazidate to the Synthesis of Peptides containing Various Functions
• Amino Acids and Peptides. X. Phosphorus in Organic Synthesis. V. On the Mechanism for the Peptide Synthesis by Diphenyl Phosphorazidate
• Amino Acids and Peptides. IX. Phosphorus in Organic Synthesis. IV. Diphenyl Phosphorazidate. A New Convenient Reagent for the Peptide Synthesis
• 19 環状ヘミアミナール構造を有する大環状デプシペプチドの合成研究 : 海洋藍藻由来のソママイドAの全合成(口頭発表の部)
• 94(P-51) 海洋産微生物由来抗炎症活性環状ペプチド、サイクロマリンAの合成研究(ポスター発表の部)
• 116(P-48) 海産藍藻由来神経毒カルキトキシンの全合成研究(ポスター発表の部)
• 30 海洋ラン藻Lyngbya majusculaから得られた神経毒kalkitoxin(口頭発表の部)
• 海産藍藻由来魚毒活性物質アンチラトキシンの全合成
• 1 海洋産チアゾール含有ポリケチド,マイコチアゾールの合成研究(口頭発表の部)
• 17 カリクリン類の合成研究(口頭発表の部)
• 87 高等植物由来の鉄輸送キレート剤ムギネ酸類の合成研究(ポスター発表の部)
• 海洋起源生物活性ペプチドの合成 (化学で探る海洋生物の謎) -- (海洋に医薬をもとめて)
• 新規有機合成反応剤の開発とその生理活性天然有機化合物合成への応用
• New Methods and Reagents in Organic Synthesis. 69. A New Synthesis of α-Amino Acid and Peptide Amides of Aromatic Amines Using a Modified Curtius Reaction with Diphenyl Phosphorazidate(Organic,Chemical)
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 57. A STEREOSELECTIVE SYNTHESIS OF A DERIVATIVE OF D-RISTOSAMINE
• TRIMETHYLSILYLDIAZOMETHANE : A USEFUL REAGENT FOR THE PREPARATION OF (Z)-1-TRIMETHYLSILYL-1-ALKENES
• New Methods and Reagents in Organic Synthesis. 60. A New Synthesis of Aromatic and Heteroaromatic Amines Using Diphenyl Phosphorazidate (DPPA)
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 46. TRIMETHYLSILYLDIAZOMETHANE : A CONVENIENT REAGENT FOR THE O-METHYLATION OF PHENOLS AND ENOLS
• New Methods and Reagents in Organic Synthesis. 26. Reductive Desulfonylation of α-Sulfonylacetates
• New Methods and Reagents in Organic Synthesis. 19. Synthesis and Rearrangement of α-Acylsulfonyldiazomethanes (α-Diazo-β-ketosulfones)
• 37 Sulfobacin類の全合成(口頭発表の部)
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 47. A GENERAL, EFFICIENT, AND CONVENIENT SYNTHESIS OF DIARYLHEPTANOIDS
• Formation and Decomposition of 1,2,3-Triazolines Prepared from Diphenyl Phosphorazidate (DPPA) and Enamines of Diaryl-Type Ketones
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 44. A NEW GENERAL EFFICIENT SYNTHESIS OF DL-[N]-GINGEROLS AND RELATIVES THROUGH DIRECT C-ACYLATION USING DIETHYL PHOSPHOROCYANIDATE (DEPC)
• New Methods and Reagents in Organic Synthesis. 35. A New Synthesis of Some Non-Steroidal Anti-Inflammatory Agents with the 2-Arylpropionic Acid Skeleton by the Use of Diphenyl Phosphorazidate (DPPA) as a 1,3-Dipole
• A Resin-promoted Williamson's Alkyl Aryl Ether Synthesis. Methylation of 2-tert-Butyl-5-methylphenol with Methyl Chloride
• Ind. -N-Alkylation of Tryptophan and Synthesis of 1-Alkyltryptophan Hydrazides
• Chemistry of Amino Acids. VII. The Synthesis and Spectral Studies of Some 2-Piperidones bearing β-Keto Ester Groups
• New Methods and Reagents in Organic Synthesis. 34. Diphenyl Phosphorazidate (DPPA) as a 1,3-Dipole. A Simple, Efficient Conversion of Akyl Phenyl Ketones to 2-Phenylalkanoic Acids
• 35 L-Tryptophan及びL-Dopaより光学活性Indole AlkaloidならびにIsoquinoline Alkaloidの生合成的不斉合成
• 異常アミノ酸を含有するペプチドの合成-ドラスタチン10を例として-
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 32. LITHIUM TRIMETHYLSILYLDIAZOMETHANE : A NEW SYNTHON FOR THE PREPARATION OF 1,2,3-TRIAZOLES
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 31. LITHIUM TRIMETHYLSILYLDIAZOMETHANE : A NEW SYNTHON FOR THE PREPARATION OF TETRAZOLES
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 30. RING ENLARGEMENT OF CYCLOALKANONES WITH BENZYLSULFONYLDIAZOMETHANE AND CONVERSION OF THE RESULTING HOMOLOGATED 2-BENZYLSULFONYLCYCLOALKANONES TO 1-BENZYLSULFONYL-1-CYCLOALKENES VIA CHELETROPIC RING CONTRA
• New Methods and Reagents in Organic Synthesis. 20. 2-Mesitylenesulfonyl diazomethane : Synthesis and Application to the Arndt-Eistert Synthesis
• New Methods and Reagents in Organic Synthesis. 17. Trimethylsilydiazomethane (TMSCHN_2) as a Stable and Safe Substitute for Hazardous Diazomethane. Its Application to the Arndt-Eistert Synthesis
• 海洋産抗腫瘍活性環状ペプチドの合成研究
• CYANOPHOSPHORYLATION OF KETONES AND ALDEHYDES USING DIETHYL PHOSPHOROCYANIDATE (DEPC)
• An Extensive Survey by the Use of High Performance Liquid Chromatography on Racemization during the Coupling of Benzyloxycarbonyl-L-phenylalanyl-L-valine with L-Proline tert-Butyl Ester
• NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 29. A PRACTICAL METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE n-PROTECTED α-AMINO ALDEHYDES AND PEPTIDE ALDEHYDES
• 78 ジフェニルリン酸アジド、ジエチルリン酸シアニドを用いるC-アシル化反応 : 2,4-ジアミノ糖プルマイシン合成への応用
• New Methods and Reagents in Organic Synthesis. 9. C-Acylation of Nitromethane with Aromatic Carboxylic Acids using Diethyl Phosphorocyanidate (DEPC)
• チオシアネートの合成法最近の進歩
• Amino Acids and peptides. XXVI. Phosphorus in Organic Synthesis. XV. Application of Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC) to the Synthesis of the N-Terminal Decapeptide of Gastric Inhibitory Polypeptide
• Amino Acids and Peptides. XXV. Phosphorus in Organic Synthesis. XIV. Application of Diphenyl Phosphorazidate (DPPA) to the Synthesis of the N-Terminal Hexapeptide of the Vasoactive Intestinal Peptide
• Studies in the Indole Series. III. Steric Inhibition of Resonance in Cycloalkan [b] indolones.
• Studies in the Indole Series. II. A General Synthesis of Cycloalkan[b]indolones
• 6 2-Acylindole Alkaloidsの合成研究 : Vobasine骨格の合成
• Studies on Optically Active Amino Acids. III. Preparation of 3-(3,4-Dihydroxyphenyl)-DL-, -D-, and-L-alanine.
• Studies on Optically Active Amino Acids. II. Partially Asymmetric Synthesis of 3-(3,4-Methylenedioxyphenyl) alanine.
• Studies on Optically Active Amino Acids. I. Preparation of 3-(3,4-Methylenedioxyphenyl)-D-, and-L-alanine.

もっと見る 閉じる

スポンサーリンク