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SYNTHESIS, CRYSTAL STRUCTURE, AND A DFT STUDY OF TERT-BUTYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE

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Abstract

Tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate is a significant intermediate of 1H-indazole derivatives. In this paper, the title compound is acquired through two substitution reactions. The structure is corroborated by FTIR, 1H and 13C NMR spectroscopy, and MS. In the meantime, the single crystal is detected by means of X-ray diffraction, calculated by exerting density functional theory (DFT), and subjected to the crystallographic and conformational analysis. The results of comparing the DFT calculated value with the X-ray diffraction value display that the optimized molecular structure does cohere with the single crystal structure ascertained via the experiment. The 98.28% stable conformer and 1.72% unstable conformers are found in the DFT calculations. Furthermore, to reveal the physicochemical features of the title compound, the molecular electrostatic potential and frontier molecular orbitals are investigated through DFT.

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Funding

This work was supported by Guizhou Provincial Natural Science Foundation ([2020]1Y393) and the Science and Technology Program Platform for Talents of Guizhou province ([2018]5781).

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Guizhou University, Guiyang, People’s Republic of China

    W. -J. Ye, D. -M. Chen, Q. -M. Wu, Y. -M. Chen, T. -H. Liao & Z. -X. Zhou

  2. Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang, People’s Republic of China

    W. -J. Ye, D. -M. Chen, Q. -M. Wu, Y. -M. Chen, D. -Z. Yang, T. -H. Liao & Z. -X. Zhou

  3. School of Chemistry and Chemical Engineering, Guizhou University, Guiyang, People’s Republic of China

    D. -Z. Yang

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Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 9, pp. 1454-1460.https://doi.org/10.26902/JSC_id79913

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Ye, W.J., Chen, D.M., Wu, Q.M. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND A DFT STUDY OF TERT-BUTYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE. J Struct Chem 62, 1357–1364 (2021). https://doi.org/10.1134/S0022476621090043

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