Studies on Quinazolines. VII. Reactions of Anthranilamide with β-Diketones; New Approaches toward the Synthesis of Tetrahydropyrido[2,1-b]quinazolin-11-one Derivatives

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概要

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• Condensation of anthranilamide and its derivatives with various 1,3-cyclohexanediones 5a, b or 2,4-pentanediones under acidic conditions produced a variety of heterocycles, leading to the synthesis of tetrahydropyrido[2,1-b]-quinazolin-11-one derivatives. Condensation of anthranilamide with 5a or 5b in the presence of p-toluenesulfonic acid at the reflux temperature of tetrahydrofuran (THF) afforded compound 6a (40%) and compound 7a (22%) or compound 6b (47%) and compound 7b (39%), respectively. However, reflux of anthranilamide with 5a or 5b in 6% ethanolic hydrogen chloride provided compounds 6a and 6b in 77% and 73% yields, respectively. Heating 7a with 5a in 6% ethanolic hydrogen chloride furnished 6a in 82.4% yield. Reaction of anthranilamide with 5c under the same conditions resulted in the formation of 11 (57%). Treatment of compounds 6a and 6b with NaBH_4 furnished 8a, b (89,87% yields), which were subsequently subjected to the Mitsunobu reaction to produce 6,7,8,9-tetrahydro-9-methyl-11H-pyrido[2,1-b]quinazolin-11-one (9a) and 6,7,8,9-tetrahydro-7,7,9-trimethyl-11H-pyrido[2,1-b]quinazolin-11-one (9b) in 56 and 72% yields, respectively. However, heating 14 with 15a in CH_3CN in the presence of p-toluenesulfonic acid furnished 19 in 31% yield. Under similar conditions, treatment of 21 with 15a provided 23a (42.4% yield), a key intermediate for the synthesis of rutaecarpine. Analogous reaction of 21 with 15b, 15c and 5a provided 22b-d in 63-99.3% yield, respectively.

• 公益社団法人日本薬学会の論文
• 1998-06-15

著者

• Wu Kuo-rong

  Institute Of Pharmacy National Defense Medical Center

• Lai Nan-yi

  Institute Of Pharmacy National Defense Medical Center

• Chern Yu-chin

  School Of Pharmacy College Of Medicine National Taiwan University

• CHERN Ji-Wang

  School of Pharmacy, College of Medicine, National Taiwan University

• CHEN Hui-Ting

  School of Pharmacy, College of Medicine, National Taiwan University

• Chen Hui-ting

  School Of Pharmacy College Of Medicine National Taiwan University

• Chern J‐w

  National Taiwan Univ. Taipei Twn

• Chern Ji-wang

  School Of Pharmacy College Of Medicine National Taiwan University No. 1 Section 1

関連論文

• Studies on Quinazolines. VII. Reactions of Anthranilamide with β-Diketones; New Approaches toward the Synthesis of Tetrahydropyrido[2,1-b]quinazolin-11-one Derivatives
• Nucleosides XI. Synthesis and Antiviral Evaluation of 5'-Alkylthio-5'-deoxy Quinazolinone Nucleoside Derivatives as S-Adenosyl-L-homocysteine Analogs

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