Thermal intramolecular cyclization of 2-ethynylpyridine N-ylides to indolizines and cyclazines.

• 土屋 隆

• 加藤 昌信

• 指田 春喜

抄録

Treatment of 2-ethynyl-1-phenacylpyridinium bromides (1a-c), prepared from 2-ethynylpyridines and phenacyl bromide, with a base, DBU, in refluxing benzene gave 3-benzoylindolizines (2), whereas heating the salts (1) in refluxing acetic acid afforded 1-benzoylindolizines (3). Upon similar treatment with the base, 2-ethynyl-6-methyl-1-phenacyl-pyridinium bromides (10a-c) gave 2-phenylcycl [3. 2. 2] azines (12), together with 3-benzoylindolizines (11). However, the reaction of 6-amino-2-ethynylpyridines (17a-c) with phenacyl bromide resulted in the formation of 1-azaindolizines (18), which were treated with the base to give 1-azacycl [3. 2. 2] azines (19). The mechanisms for these intramolecular cyclization via pyridine N-ylide intermediates are discussed.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 32 (11), 4666-4669, 1984

  公益社団法人 日本薬学会

キーワード

• 1-azacycl [3. 2. 2] azine

詳細情報

• CRID: 1390001204165569792
• NII論文ID: 130003769516
• DOI: 10.1248/cpb.32.4666
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/32/11/32_11_4666/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可