Gold(III)-Catalyzed Selective Cyclization of Alkynyl Quinazolinone- Tethered Pyrroles: Synthesis of Fused Quinazolinone Scaffolds
Gold(III)-Catalyzed Selective Cyclization of Alkynyl Quinazolinone- Tethered Pyrroles: Synthesis of Fused Quinazolinone Scaffolds
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金 (III) 催化的炔基喹唑啉酮系吡咯的选择性环化：稠合喹唑啉酮支架的合成
DOI：
10.1021/acs.joc.8b00168
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Gui-Fa Su
中科院分区：
文献类型：
--
作者：
Lin-Su Wei;Guo-Xue He;Xiang-Fei Kong;Cheng-Xue Pan;Dong-Liang Mo;Gui-Fa Su
通过金催化的炔基喹唑啉系链吡咯选择性氢化反应，合成了一系列1,2-和2,3-融合的喹唑啉酮，收率很高。研究表明，n1 -炔基喹唑啉系吡咯通过1,3重排和顺序的6-外三环化得到1,2-融合的喹唑啉酮，而n3 -炔基喹唑啉系吡咯通过6-外二环化直接得到7-内二环化得到2,3-融合的喹唑啉酮。以市售的邻氨基苯甲酰胺为原料，分三步制得克级融合喹唑啉酮。
A series of 1,2- and 2,3-fused quinazolinones have been synthesized in good to excellent yields through gold-catalyzed selective hydroarylations of alkynyl quinazolinone-tethered pyrroles. The studies revealed that 1,2-fused quinazolinones were obtained through a 1,3-rearrangement and sequential 6-exo-trigcyclization of N1-alkynyl quinazolinone-tethered pyrroles, while N3-alkynyl quinazolinone-tethered pyrroles went through 6-exo-digor 7-endo-digcyclizations directly to afford 2,3-fused quinazolinones. The fused quinazolinones could be prepared at gram scale in three steps from commercialortho-aminobenzamide.