The first entry to pyrrolo[2,3-c]quinoline-2,4(3aH,5H)-diones

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• 作者：Stanislav Kafka ; Antoní ; n Klá ; sek ; Ji&#x159 ; í ; Polis ; Veronika Rosenbreierová ; Ctibor Palí ; k ; Vladimí ; r Mrkvič ; ka ; Janez Koš ; mrlj
• 关键词：Pyrrolo[2 ; 3-c]quinolones ; Quinolinones ; Wittig olefination ; Mechanism ; NMR
• 刊名：Tetrahedron
• 出版年：2008
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：5 May 2008
• 卷：64
• 期：19
• 页码：4387-4402
• 文件大小：486 K

摘要

Wittig olefination of 3-aminoquinoline-2,4(1H,3H)-diones rong>1rong> with ethyl (triphenylphosphoranylidene)acetate (Ph₃Prc="http://www.sciencedirect.com/scidirimg/entities/dbnd" alt="double bond; length as m-dash" title="double bond; length as m-dash" border="0">CHCO₂Et) afforded (E)-3-amino-4-ethoxycarbonylmethylene-1,2,3,4-tetrahydro-2-quinolones (E)-rong>2rong> and pyrrolo[2,3-c]quinoline-2,4(3aH,5H)-diones rong>3rong>. An alternative approach for the synthesis of rong>3rong> via 3-bromoacetamidoquinoline-2,4(1H,3H)-diones rong>7rong>, their corresponding triphenylphosphonium salts rong>8rong>, and ylides rong>Arong> that undergo intramolecular Wittig reaction, was investigated. Under the applied reaction conditions, the phosphonium salts rong>8rong> and ylides rong>Arong> are so unstable that they partly decompose to 3-acetamidoquinoline-2,4(1H,3H)-diones rong>9rong> during the synthesis of rong>3rong>.