The Triflic Acid-Mediated Cyclization Reactions of N-Cinnamoyl-1-Naphthylamines

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• 作者：Frank D. King ; Abil E. Aliev ; Stephen Caddick ; Derek A. Tocher
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：November 1, 2013
• 年：2013
• 卷：78
• 期：21
• 页码：10938-10946
• 全文大小：345K
• 年卷期：v.78,no.21(November 1, 2013)
• ISSN：1520-6904

文摘

N-Cinnamoyl-1-naphthylamines undergo a cyclization reaction with triflic acid to form 4-phenyl-3,4-dihydro-1H-naphth[1,8-bc]azepin-2-ones and 4-phenyl-3,4-dihydro-1H-benzo[h]quinolin-2-ones. However, the N-benzyl analogues also undergo a unique cascade reaction to form novel heptacyclic structures via a 1,2-addition followed by a 4-addition to the naphthalene. With an electron-rich N-benzyl substituent, the heptacycle is the sole product.