Preparation and Reactions of 3-(Aminomethylene)-3H-indoles
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概要
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A series of 3-(aminomethylene)-3H-indoles (1a-e and 6a-8a) was prepared by the condensation of 3-indolecarbaldehydes (2-5) with secondary amines. Among them, 3-(1-pyrrolidinylmethylene)-3H-indoles (1a and 6a-8a) were obtained as stable colorless prisms, while 3-(piperidinomethylene)-3H-indole (1b) and 3-(morpholinomethylene)-3H-indole (1c) readily polymerized in refluxing benzene. Reaction of 1 with electrophiles, such as alkyl and acyl halides, gave 1-substituted 3-aminomethylene-3H-indolium salts, which were converted to the corresponding 1-substituted 3-indolecarbaldehydes by hydrolysis. Reaction of 1 with active methylene compounds proceeded under mild reaction conditions to afford the corresponding condensation products in good yields. Successive reaction of 1 with electrophiles and nucleophiles provided a convenient route to 1,3-disubstituted indole derivatives.
- 1980-06-25
著者
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米田 直人
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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守屋 多聞
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.,
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米田 直人
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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萩尾 克明
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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守屋 多聞
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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萩尾 克明
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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米田 直人
Research Laboratory of Applied Biochemistry
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米田 直人
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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