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Base Induced Cyclobutenone Rearrangements and Its Application in the Synthesis of Aromatic Amines
- Han, Xiaodan, Fu, Jianping, Hu, Juwu, Xiong, Wei, Wang, Huibin, Wu, Lei
- Tetrahedron letters 2019
- aromatic amines, chemical reactions, chemical structure, regioselectivity, toluene
- A series of fully substituted 2-pyridone 2 and functionalized α-pyrones 3 are synthesized starting from cyclobutenones 1 under a base-promoter in toluene at 80 ℃. This rearrangement is complimentary to the previously reported ring expansion of cyclobutenones, providing a divergent synthesis of corresponding products from the same precursor 1. In addition, α-pyrones 3 has also been applied to the synthesis of aromatic amines 7 in good yields (64–83%) and in a highly regioselective manner via D-A reaction under mild conditions.