I2-DMSO-Mediated Transannulation of Benzo[d]isoxazol-3-amine: Direct Access to 2,4,5-Substituted Pyrimidine Derivatives

作者:Liu, Jin-Yi; Zhuang, Shi-Yi; Tang, Yong-Xing; Chen, Xiang-Long; Zhou, You; Wu, Yan-Dong; Zheng, Kai-Lu*; Wu, An-Xin*
来源:Journal of Organic Chemistry, 2023, 88(16): 12000-12012.
DOI:10.1021/acs.joc.3c01327

摘要

An I-2-DMSO-mediated multicomponent [3+1+2]cascade annulationreaction using aryl methyl ketones, enaminones, and benzo[d]isoxazol-3-amine as substrates has been developed. Thismetal-free reaction involved the transannulation of benzo[d]isoxazol-3-amines with the formation of two C-Nbonds and a C-C bond in one pot. Notably, a pyrimidine ringwith a 1,4-dicarbonyl scaffold could efficiently transform into apyrimido[4,5-d]pyridazine skeleton. The phenolichydroxyl group of the target product could undergo further modificationwith pharmaceuticals, demonstrating the utility of this method.

  • 单位
    1; 广东医学院