4-Nitro-及び5-Nitro-<I>N</I>-(2-nitroxyethyl) nicotinamideの合成

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書誌事項

タイトル別名
  • Synthesis of 4-Nitro- and 5-Nitro-<I>N</I>-(2-nitroxyethyl) nicotinamide
  • 4-Nitro-及び5-Nitro-N-(2-nitroxyethyl)nicotinamideの合成
  • 4 Nitro オヨビ 5 Nitro N 2 nitroxyethyl ni
公開日
1986
DOI
  • 10.1248/yakushi1947.106.10_872
公開者
公益社団法人 日本薬学会

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説明

The following results were obtained during synthetic studies of 4-and 5-nitro derivatives (7 and 8) of N-(2-nitroxyethyl) nicotinamide, a new antianginal drug (I).<BR>1) Nicotinic acid 1-oxide (1a) and its derivatives (1b, c, d) resisted γ-nitration, whereas the methyl ester (1b) underwent β-nitration on treatment with N-nitropyridinium tetrafluoroborate at room temperature in dichloromethane. 2) 4-Nitronicotinic acid 1-oxide (2a) was successfully converted to the methyl ester (2b) and the amide (2c) in good yields by treatment with diazomethane and through the active ester with 1-hydroxybenzotriazole, respectively. 3) Deoxygenation of 2b and 2c was smoothly effbcted with phosphoryl bromide, but that of 2a gave no 4-nitronicotinic acid. 4) On the basis of these findings, 7 and 8 were synthesized starting from 2a through the amide 2f, and from 5-nitronicotinic acid, respectively.

収録刊行物

  • 薬学雑誌

    薬学雑誌 106 (10), 872-877, 1986

    公益社団法人 日本薬学会

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