Studies of Nitriles. XI. Preparation and Chemistry of Schiff Bases of ADAN, 2-Amino-3,3-dichloroacrylonitrile. A highly Effective Conversion into 2-Substituted-4 (5)-chloroimidazole-5 (4)-carbaldehydes

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概要

• 論文の詳細を見る

• Schiff bases of 2-amino-3,3-dichloroacrylonitrile (ADAN) have been prepared in excellent yields by condensation of ADAN with various aldehydes under mild conditions. These Schiff bases (2,3,4) are highly reactive polyfunctional compounds and useful synthetic intermediates : the chlorine atoms of Schiff base 2e react with various nucleophiles such as alkoxides, mercaptides, and primary and secondary amines giving the corresponding 3,3-dialkoxy-, 3,3-bis (substituted mercapto)-, and 3,3-bis (substituted amino)-derivatives (7,8,and 10), respectively. Reduction of Schiff base 2e with zinc powder under mild conditions resulted in formation of the monochloro derivative 5. With anhydrous hydrogen chloride in ether, these Schiff bases underwent smooth cyclization to new 4 (5)-chloro-5(4)-dichloromethylimidazoles 11,which in turn were converted into 4 (5)-chloro-imidazole-5 (4)-carbaldehydes 12 in excellent yields upon hydrolysis.

• 公益社団法人日本薬学会の論文
• 1976-05-25

著者

• 橋本 直人

  Central Research Division Takeda Chemical Industries Ltd.

• 橋本 直人

  Chemistry Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 松村 興一

  Central Research Division, Takeda Chemical Industries, Ltd.

• 松村 興一

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 栗谷 雅明

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 島津 浩

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 島津 浩

  Pharmaceutical Research Division Pharmaceutical Research Laboratories Iii Takeda Chemical Industires

• 栗谷 雅明

  Chemical Research Laboratories Central Research Division Takeda Chemical Industries Ltd.

• 松村 興一

  Central Research Division Takeda Chemical Industries Ltd.

関連論文

• Synthetic Studies on Condensed-Azole Derivatives. III. Synthesis and Anti-asthmatic Activities of C-Substituted Alkyl Side Chain Derivatives of ω-Sulfamoylalkylthioimidazo[1,2-b]pyridazines and Related Compounds
• Chemical Modification of Ansamitocins. III. Synthesis and Biological Effects of 3-Acyl Esters of Maytansinol
• Chemical Modification of Ansamitocins. II. Synthesis of 3-Epimaytansionoids via 3-Maytansinones
• Chemical Modification of Ansamitocins. I. Synthesis and Properties of 4,5-Deoxymaytansinoids
• Studies on Fluorinated Pyrimidines. IV. Stereochemistry of 6-Alkoxy-5-fluoro-5,6-dihydrouracils and 5-Alkoxycarbonyl-5-fluoro-6-substituted-5,6-dihydrouracils
• Studies on Fluorinated Pyrimidines. III. Synthesis of 1-Acyl- and 1,3-Diacyl-5-alkoxycarbonyl-5-fluoro-6-substituted-5,6-dihydrouracils
• Studies on Fluorinated Pyrimidines. II. Synthesis and Antitumor Activity of 5-Fluoro-6-substituted-5,6-dihydrouracil-5-carboxylic Acid Derivatives
• Studies on Fluorinated Pyrimidines. I. A New Method of Synthesizing 5-Fluorouracil and Its Derivatives
• Studies of Nitriles. XI. Preparation and Chemistry of Schiff Bases of ADAN, 2-Amino-3,3-dichloroacrylonitrile. A highly Effective Conversion into 2-Substituted-4 (5)-chloroimidazole-5 (4)-carbaldehydes
• Studies of Nitriles. X. Synthesis and Reactions of 2-Acylamino-3,3-bis-(substituted mercapto) acrylonitriles and Their Derivatives. A New Synthesis of 2-Substituted-5-(substituted mercapto) oxazole-4-carbonitriles and Their Derivatives
• Studies of Nitriles. IX. Reactions of 2-Acetylamino-3,3-dichloroacrylic Amide and-N-acylamide with Aliphatic Amines. (2). Syntheses of Some α, α-Diamino Acid Derivatives
• Studies of Nitriles. VIII. Reactions of N-Acyl Derivatives of 2-Amino-3,3-dichloroacrylonitrile (ADAN) with Amines. (1). A New Synthesis of 2-Substituted-5-(substituted amino) oxazole-4-carbonitriles and-4-N-acylcarboxamides
• Studies of Nitriles. VII. Synthesis and Properties of 2-Amino-3,3-dichloroacrylonitrile (ADAN)

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