PubAg

Main content area

Base Induced Cyclobutenone Rearrangements and Its Application in the Synthesis of Aromatic Amines

Author:
Han, Xiaodan, Fu, Jianping, Hu, Juwu, Xiong, Wei, Wang, Huibin, Wu, Lei
Source:
Tetrahedron letters 2019
ISSN:
0040-4039
Subject:
aromatic amines, chemical reactions, chemical structure, regioselectivity, toluene
Abstract:
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.
Agid:
6741279