A Novel Synthesis of 1,2,3,4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N-[(phenylsulfinyl)propyl]formamide
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概要
- 論文の詳細を見る
A synthesis of 1,2,3,4-tetrahydroquinolines (TQs) 13 with two and three methoxyl groups on the benzene ring, was achieved via intramolecular cyclization of N-aryl-N-[(phenylsulfinyl)propyl]formamides 7 utilizing the Pummerer reaction as a key step. The reaction was carried out by using trifluoroacetic anhydride (TFAA)(method A) or TFAA-BF_3・Et_2O (method B). The cyclization to 4-PhSTQs 8 proceeded effectively when the reaction center at the benzene ring was electronically activated by a methoxyl group. In the reaction of sulfoxide 7e having two OMe groups in the ortho- and para-positions, a different cyclization reaction leading to 1,5-benzothiazepine derivative 9 was observed, indicating that the high uncleophilicity of the benzene ring caused the unexpected reaction prior to cyclization to 4-PhSTQs 8. This route starting from methoxyanilines provides an efficient and convenient method of TQ synthesis.
- 公益社団法人日本薬学会の論文
- 1999-09-15
著者
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佐野 武弘
昭和薬科大学
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佐野 武弘
Showa Pharmaceutical Univ. Tokyo Jpn
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SANO Takehiro
Showa College of Pharmaceutical Sciences
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TODA Jun
Showa College of Pharmaceutical Sciences
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Toda J
Showa Coll. Pharmaceutical Sci. Tokyo Jpn
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SAKAGAMI Michiya
Showa Pharmaceutical University
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Sakagami M
Shionogi Research Laboratories Shionogi & Co. Ltd.
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