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Synthesis of 6a,6b,13,13a-tetrahydro-6H-5-oxa-12a-azadibenzo[a,g]fluorene derivatives via cycloaddition reactions of isoquinolinium salts with 3-nitrochromenes

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Abstract

An efficient and diastereoselective synthetic procedure for functionalized 6a,6b,13,13a-tetrahydro-6H-5-oxa-12a-azadibenzo[a,g]fluorene derivatives was successfully developed by the cycloaddition reaction of isoquinolinium salts and 3-nitrochromenes with triethylamine as base in ethanol at room temperature. \({}^{1}\hbox {H}\) NMR data and single crystal structures confirm the production and isolation of a single stereoisomer.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Grant No. 21172189) and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We also want to give thanks to Analysis and Test Centre of Yangzhou University for providing instruments for analysis.

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Authors and Affiliations

  1. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225002, People’s Republic of China

    Jun Fang & Chao-Guo Yan

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  1. Jun Fang
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  2. Chao-Guo Yan
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Correspondence to Chao-Guo Yan.

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Fang, J., Yan, CG. Synthesis of 6a,6b,13,13a-tetrahydro-6H-5-oxa-12a-azadibenzo[a,g]fluorene derivatives via cycloaddition reactions of isoquinolinium salts with 3-nitrochromenes. Mol Divers 18, 91–99 (2014). https://doi.org/10.1007/s11030-013-9489-z

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