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Microwave-assisted facile construction of quinoxalinone and benzimidazopyrazinone derivatives via two paths of post-Ugi cascade reaction

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Abstract

A facile and efficient route to synthesize quinoxalinone and benzimidazopyrazinone was developed via two paths of a post-Ugi cascade reaction. By simply alternating the order of nucleophilic substitution reactions, both heterocycles could be accessed selectively from the same Ugi adduct. Microwave-assisted synthesis protocol provided these compounds with one purification procedure for three steps. These two scaffolds with more possible spaces for further modifications provide great benefit toward combinatorial and medicinal chemistry campaigns.

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Acknowledgements

The authors would like to thank the Chongqing Research Program of Basic Research and Frontier Technology (cstc2015jcyjA1328 and cstc2015zdcy-ztzx0191) and the Scientific Research Foundation of the Chongqing University of Arts and Sciences (Grant Nos. R2013XY01, R2013XY02 and M2016ME11). We would also like to thank Ms H.Z. Liu for obtaining the LC/MS and NMR data.

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Authors and Affiliations

  1. Chongqing Engineering Laboratory of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators as Innovative Medicine, IATTI, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, China

    Gui-Ting Song, Yong Li, Jia Xu, Zhi-Gang Xu, Yong Ding, Jie Lei & Zhong-Zhu Chen

  2. Key Laboratory for Asymmetric Synthesis and Chiral Technology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China

    Gui-Ting Song & Jie Lei

  3. University of Chinese Academy of Sciences, Beijing, 100049, China

    Gui-Ting Song, Jie Lei & Jin Zhu

  4. Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR, 72205, USA

    Nicholas McConnell

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  1. Gui-Ting Song
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  8. Jin Zhu
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Correspondence to Jin Zhu or Zhong-Zhu Chen.

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Song, GT., Li, Y., Xu, J. et al. Microwave-assisted facile construction of quinoxalinone and benzimidazopyrazinone derivatives via two paths of post-Ugi cascade reaction. Mol Divers 23, 137–145 (2019). https://doi.org/10.1007/s11030-018-9855-y

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