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Synthesis, Spectroscopic Properties and DFT Calculation of Novel Pyrrolo[1′,5′-a]-1,8-naphthyridine Derivatives through a Facile One-pot Process

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Abstract

Novel pyrrolo[1′,5′-a]-1,8-naphthyridine compounds (L1-L4) have been synthesized through a facile one-pot process by the reaction of the corresponding 1,8-naphthyridines with aliphatic anhydride. The structures were established by spectroscopic data. Further, X-ray crystal analysis of 7-diacetamino-2,4-dimethy-1,8-naphthyridine (L1) identifies its molecular structure and reveals π- π stacking. The synthetic mechanisms for L2, L3 were studied by density functional theory calculations. And a comprehensive study of spectroscopic properties involving experimental data and theoretical studies is presented. L1 exhibited electronic absorption spectrum with λ max at ∼320 nm. L2-L4 exhibited similar electronic absorption spectra with λ max at ∼390 nm that is tentatively assigned to π→π* transition. The assignment was further supported by density functional theory (DFT) calculations.

Novel pyrrolo[1′,5′-a]-1,8-naphthyridine compounds have been synthesized through a facile one-pot process. Further, X-ray crystal analysis and spectroscopic properties are presented.

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Acknowledgements

This work is supported by the National Natural Science Foundation of China (61361002, 21262049 and 21461007), the “Chun Hui” Plan of Chinese Ministry Education (Z2011125), the Scientific Research Foundation of Education Department of Yunnan Province (2013FZ121), the General Program of Yunnan Provincial Education Departmen (2015Y455), the Chemistry of Key Construction Disciplines for Master Degree Program in Yunnan (HXZ1303) and the Educational Reform Program of Honghe University (JJJG1412).

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Authors and Affiliations

  1. School of Science, Honghe University, Mengzi, Yunnan, 661199, P. R. China

    GAO-ZHANG GOU, BO ZHOU, HE-PING YAN, YONG HONG & WEI LIU

  2. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650092, P. R. China

    SHAO-MING CHI

  3. College of Pharmaceutical Science and Chemistry, Dali University, Dali, Yunnan, 671000, P. R. China

    CHAO-YONG MANG

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  1. GAO-ZHANG GOU
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Correspondence to CHAO-YONG MANG.

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Supplementary information associated with this article, i.e., experimental procedures, characterization data, computational details, additional spectral data, and crystallographic data (CIF) are available at www.ias.ac.in/chemsci.

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GOU, GZ., ZHOU, B., YAN, HP. et al. Synthesis, Spectroscopic Properties and DFT Calculation of Novel Pyrrolo[1′,5′-a]-1,8-naphthyridine Derivatives through a Facile One-pot Process. J Chem Sci 128, 1813–1821 (2016). https://doi.org/10.1007/s12039-016-1163-4

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