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An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction

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Abstract

A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3H)-one was disclosed in DMF catalyzed by CuI/l-proline in the presence of Cs2CO3. This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones in good yields.

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Acknowledgements

This work was financially supported by NSFC of China (No. 21702078), Natural Science Foundation of Jiangsu Higher Education Institution (17KJA150003), the Priority Academic Program Development of Jiangsu Higher education Institution, and TAPP.

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Authors and Affiliations

  1. School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Wei-Qing Miao, Jian-Quan Liu & Xiang-Shan Wang

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  1. Wei-Qing Miao
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  2. Jian-Quan Liu
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  3. Xiang-Shan Wang
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Correspondence to Xiang-Shan Wang.

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Miao, WQ., Liu, JQ. & Wang, XS. An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction. Monatsh Chem 150, 1305–1315 (2019). https://doi.org/10.1007/s00706-019-02430-6

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  • DOI: https://doi.org/10.1007/s00706-019-02430-6

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