Triazolo[4,5-d]pyrimidines. X. Halogen-Metal Exchange Reaction of 7-Halo-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidines with Butyllithium

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概要

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• The amino group at the 7-position on the 3H-1,2,3-triazolo[4,5-d]pyrimidine ring was converted into halogen atoms by treatment with isopentyl nitrite in halomethanes, in satisfactory yields. The halogen-metal exchange reaction between 7-iodo-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (2) and butyllithium in the presence of N, N, N', N'-tetramethylethylenediamine proceeded, giving the 7-lithio compound (9). The lithio compound (9) reacted smoothly with electrophiles to give the corresponding 7-substituted compounds (15-18). On the other hand, the reaction of 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (1) with butyllithium gave the ring fission product, 5-amino-1-phenyl-1H-1,2,3-triazole-4-carbonitrile (14).

• 社団法人日本薬学会の論文
• 1991-11-25

著者

• 東野 武郎

  School Of Pharmaceutical Sciences University Of Shizuoka

• 加藤 広之

  School Of Pharmaceutical Sciences University Of Shizuoka

• 丹治 健一

  School of Pharmaceutical Sciences, University of Shizuoka

• 丹治 健一

  School Of Food & Nutritional Sciences University Of Shizuoka

関連論文

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• N-N BOND CLEAVAGE OF 1-CHLOROPHTHALAZINE BY THE REACTION WITH YNAMINES
• Condensed Pyridazines. VIII. Reaction of Diazolopyridazines with Ynamine. Formation of Ben-zodiazoles and Diazolodiazocines
• Phthalazines. XV. Ring Transformation of Phthalazines into Naphthalenes by Means of Inverse-Electron-Demand Diels-Alder Reaction
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• Condensed Pyridazines. VII. : Reaction of 7-(Methylsulfonyl)-1-phenyl-1H-imidazo[4,5-d]pyridazine with Nucleophiles
• Condensed Pyridazines. VI. Reaction of 7-(Methylsulfonyl)-1-phenyl-1H,2,3-triazolo[4,5-d]pyridazine with Carbanions and Enamines(Organic,Chemical)
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• Reaction of Ethyl 4-Halo-3-oxobutanoate with Diethyl Malonate, Methyl Cyanoacetate, and Malononitrile
• Catalytic Action of Azolium Salts. IV. Preparations of 4-Aroylquinazolines and 4-Aroyl-1H-pyrazolo[3,4-d]pyrimidines by Catalytic Action of 1,3-Dimethylimidazolium Iodide
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• Purines. VI. Reactions of 2-Chloro- and 2-(Methylsulfonyl)-9-phenyl-9H-purines with Nucleophiles(Organic,Chemical)
• Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
• Studies on Pyrimidine Derivatives. XXXIII. Synthesis of Alkyl Pyrimidinyl Ketones by Means of Nitrosation of Alkylpyrimidines
• Studies on Pyrimidine Derivatives. XXVII. Synthesis of 2- and 4-Pyrimidinyl Ketones by Means of the Hydration of Alkynylpyrimidines
• Studies on Pyrimidine Derivatives. XXVI. Synthesis of Derivatives containing a 1,3-Dicarbonyl Side Chain
• Studies on Pyrimidine Derivatives. XXV. Reaction of Pyrimidinyl Aldehydes and Ketones with Witting Reagents
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