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Gold(I)-Catalyzed Formal Intramolecular Dehydro-Diels–Alder Reaction of Ynamide-ynes: Synthesis of Functionalized Benzo[b]carbazoles
Organic Letters ( IF 5.2 ) Pub Date : 2018-05-16 00:00:00 , DOI: 10.1021/acs.orglett.8b01145
Wei Xu 1 , Gaonan Wang 1 , Xin Xie 1 , Yuanhong Liu 1
Affiliation  

A gold-catalyzed cycloisomerization of ynamide-ynes via a formal dehydro-Diels–Alder reaction has been developed, providing an attractive route to diversely substituted benzo[b]carbazoles. The reaction likely proceeds via regioselective attack of the pendant alkyne moiety to a keteniminium ion intermediate followed by benzannulation. The method offers several advantages such as high efficiency, mild reaction conditions, and wide functional group tolerance and serves as a highly useful complement to the thermal DDA reactions of ynamide-ynes.

中文翻译:

金(I)催化的亚酰胺酰胺的形式化分子内脱氢-狄尔斯-阿尔德反应:官能化的苯并[ b ]咔唑的合成

已经开发了通过正式的脱氢-狄尔斯-阿尔德反应的金催化的炔基-炔烃环异构化反应,为各种取代的苯并[ b ]咔唑提供了诱人的途径。该反应可能是通过炔烃侧基区域选择性地攻击酮亚胺离子中间体并随后进行苯环化而进行的。该方法具有许多优点,例如高效,温和的反应条件和宽泛的官能团耐受性,可作为对乙酰胺炔炔的热DDA反应的高度有用的补充。
更新日期:2018-05-16
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