Reaction of N-Aminopyridinium Derivatives. III. Synthesis of s-Triazolo [1, 5-α]-pyridine Ring.
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N-Aminopyridinium salt (I) was reacted with cyanide ion in water at room temperature to give 2-(4-pyridyl)-s-triazolo [1, 5-α] pyridine (IV). In alkaline medium I exists as an equilibrium mixture with the ylide type, N-iminopyridine (II) which was reacted with several nitrile compounds to produce s-triazolo [1, 5-α] pyridine derivatives by 1, 3 dipolarcyclo addition. This novel triazole ring could also be synthesized by ring closure of 1, 2-diaminopyridinium salt with a carboxylic acid, acid chloride or acid anhydride. Reaction of N-methylaminopyridinium salt (XIII) or N-acetamidopyridinium salt (XIV) with cyanide ion did not afford any 1, 3-dipolar cycloaddition products. Explanation for the difference in reactivity among I, XIII and XIV was attempted from each pKa' values.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 14 (5), 506-512, 1966
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679145524096
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- NII論文ID
- 110003619886
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DyaF28XksVOltLo%3D
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- ISSN
- 13475223
- 00092363
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- PubMed
- 5939665
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- 本文言語コード
- en
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- データソース種別
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- JaLC
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- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可