Increasing appendage diversity on 3,4-dihydro-3-oxo-2H-1,4-benzoxazines via Aphos-Pd(OAc)₂-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides

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• 作者：Gongli Yu ; Yu Zheng ; Jinlong Wu ; Wei-Min Dai
• 关键词：2-Aminophenols ; Appendage diversity ; Aryl chlorides ; 1 ; 4-Benzoxazines ; Microwave ; Suzuki&ndash ; Miyaura cross-coupling
• 刊名：Tetrahedron
• 出版年：2 December, 2013
• 年：2013
• 卷：69
• 期：48
• 页码：10488-10496
• 全文大小：555 K

文摘

A library of 32 members of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines has been synthesized from two substituted 2-aminophenols via microwave-assisted one-pot regioselective annulation of 2-bromoalkanoates and subsequent Suzuki-Miyaura cross-coupling of the chloro-substituted scaffolds. The latter transformation was carried out using our Aphos-Pd(OAc)₂ catalyst and the coupling of the aryl chlorides with arylboronic acids proceeded under mild reaction conditions at 60-80聽掳C in THF-H₂O (10:1) in the presence of K₃PO₄路3H₂O as the base to furnish the corresponding biaryl products in 80-98% yields.