Synthesis of 4-Hydroxymethylene-1,3(2H, 4H)-iso-quinolinediones and Related Compounds

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概要

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• Vilsmeier-Haack reactions of 1,3(2H, 4H)-isoquinolinediones (1a, b) with dimethylformamide and POCl_3 afforded 4-hydroxymethylene-1,3(2H, 4H)-isoquinolinediones (2a, b) in good yields.Similar reactions of 1a, b using formanilides instead of N, N-dimethylformamide gave the 4-anilinomethylene compounds (3a, b). Chlorinations of 2a, b with POCl_3 in CHCl_3 or tetrahydro-furan gave the 4-chloromethylene compounds 4a, b. Treatment of 2a with POCl_3 in the absence of solvent afforded 4a and 1,3-dichloro-4-(dichloromethyl)isoquinoline (5). Compound 2b reacted with various amines including ketone reagents to form the corresponding 4-aminomethylene compounds 7a-e, and 7a-e as well as 3a, b could also be prepared from the reactions of 4b with appropriate amines. Catalytic hydrogenation of 2b resulted in the formation of 2,4-dimethyl-1,3(2H, 4H)-isoquinolinedione (8) and 2,2', 4,4'-tetramethyl[4,4'-biisoquinoline]-1,1', 3,3'(2H, 2'H-4H, 4'H)-tetrone (9).

• 社団法人日本薬学会の論文
• 1986-07-25

著者

• 乙益 寛隆

  Hoshi College of Pharmacy

• 東山 公男

  Faculty of Pharmaceutical Sciences, Hoshi University

• 乙益 寛隆

  Faculty of Pharmaceutical Sciences, Hoshi University

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 東山 公男

  星薬科大学

• 外山 美代子

  Department of Pharmacy, College of Science and Technology, Nihon University

• 東山 公男

  Faculty Of Pharmaceutical Science Hoshi University

• 外山 美代子

  Department Of Pharmacy College Of Science And Technology Nihon University

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