A Concise Domino Synthesis of Benzo-1,4-heterocycle Compounds via a Piancatelli/C-N Coupling/Michael Addition Process Promoted by La(OTf)(3)

作者：Liu, Jinqian; Shen, Qiang; Yu, Jianjun^*; Zhu, Mengyun; Han, Jianwei; Wang, Limin

来源：European Journal of Organic Chemistry, 2012, 2012(35): 6933-6939.

DOI：10.1002/ejoc.201200962

• Nitrogen heterocycles
• Oxygen heterocycles
• Domino reactions
• Rearrangement
• Lanthanides

A La(OTf)(3)-catalyzed domino method has been developed to synthesize the cis-1,4-benzoxazine derivatives from 2-furyl-carbinols 1 and o-aminophenol derivatives, by a Piancatelli/C-N coupling/Michael addition process. A wide array of substrates could be used to give the desired products in good yields. Since this method involves simple reaction conditions and short reaction times, and has a broad substrate scope, it is particularly attractive for the efficient development of libraries of biologically relevant 1,4-benzoxazine derivatives. Furthermore, a similar strategy was also successfully applied to form 1,2,3,4-tetrahydroquinoxaline derivatives from 1 and N-substituted o-diaminobenzenes.

• 出版日期2012-12
• 单位华东理工大学