Studies on the Smiles Rearrangement. XIV. Novel Reactions of 1, 3-Dimethyl-5-nitro-6-chlorouracil with 2-Aminothiophenol

• 牧 敬文

• 平光 時幸

• 鈴木 己喜男

抄録

The reaction of 1, 3-dimethyl-5-nitro-6-chlorouracil with 2-aminothiophenol in benzene containing an excess of triethylamine gave 1, 3-dimethyl-10H-pyrimido (5, 4-b) (1, 4) benzothiazine-2, 4 (1H, 3H) dione quantitatively via the Smiles rearrangement. The reaction in acetic acid, however, resulted in the formation of 2-methyl-4-nitropyrimido (4, 3-b) benzothiazoline-1, 3 (2H, 10H)-dione in 78% yield, involving an unusual uracil-ring cleavage which appears to occur in a benzothiazoline intermediate in the course of the acid-catalized Smiles rearrangement.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 22 (6), 1265-1268, 1974

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390001204177693696
• NII論文ID: 110003633270
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.22.1265
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/22/6/22_6_1265/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1975025453
• 本文言語コード: en
• データソース種別:
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  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可