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Syntheses and Crystal Structures of Two 2H-dibenzo[e, g]indazoles

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Abstract

In this paper, two 2H-dibenzo[e, g]indazoles, 6-methoxy-9-isopropoxy-2H-dibenzo[e, g]indazole(1) and 6-fluoro-9-methoxy-2H-dibenzo[e, g]indazole(2) have been one-pot synthesized from the corresponding isoflavones by two dehydration processes. They have been characterized by IR, NMR, HRMS and single crystal X-ray diffraction. Single crystal X-ray diffraction analyses show that 1 crystallizes in the orthorhombic space group P 212121, and 2 in the monoclinic space group P 21. For both structures, intermolecular hydrogen bonding, π…π and C−H…π interactions play an important role in the packing of the molecules.

Graphic Abstract

Two 2H-dibenzo[e, g]indazoles, 6-methoxy-9-isopropoxy-2H-dibenzo[e, g]indazole and 6-fluoro- 9-methoxy-2H-dibenzo[e, g]indazole have been one-pot synthesized from the corresponding isoflavones by two dehydration processes. Single crystal X-ray diffraction analyses show that hydrogen bonding, π…π and C–H…π interactions are present in both structures.

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References

  1. Shi HP, Chen L (2000) Chin J Appl Chem 17:420

    CAS  Google Scholar 

  2. Jarnes DR, Baker DR, Mielich SD, Michaely WJ, Knudsen SG, Mathews JM (1995) Us Patent US 5444038A

  3. Rosati O, Curini M, Marcotullio MC, Macchiarulo A, Perfumi M, Mattioli L, Rismondo F, Cravotto G (2007) Bioorg Med Chem 15:3463

    Article  CAS  Google Scholar 

  4. Minu M, Thangadurai A, Wakode SR, Agrawal SS, Narasimhan B (2009) Bioorg Med Chem Lett 19:2960

    Article  CAS  Google Scholar 

  5. Zhao Q, Du J, Gu H, Teng X, Zhang Q, Qin H, Liu N (2007) Pancreas 34:242

    Article  Google Scholar 

  6. Meyers MJ, Arhancet GB, Hockerman SL, Chen X, Long SA, Mahoney MW, Rico JR, Garland DJ, Blinn JR, Collins JT, Yang S, Huang H, McGee KF, Wendling JM, Dietz JD, Payne MA, Homer BL, Heron MI, Reitz DB, Hu X (2010) J Med Chem 53:5979

    Article  CAS  Google Scholar 

  7. Lyn HJ, Gill A, Oscar B, Catherine B (2009) J Med Chem 52:1219

    Article  Google Scholar 

  8. Souers AJ, Gao J, Brune M, Bush E, Wodka D, Vasudevan A, Judd AS, Mulhern M, Brodjian S, Dayton B, Shapiro R, Hernandez LE, Marsh KC, Sham HL, Collins CA, Kym PR (2005) J Med Chem 48:1318

    Article  CAS  Google Scholar 

  9. Gerpe A, Aguirre G, Boiani L, Cerecetto H, Gonzalez M, Olea-Azar C, Rigol C, Maya JD, Morello A, Piro OE, Aran VJ, Azqueta A, de Cerain AL, Monge A, Rojas MA, Yaluff G (2006) Bioorg Med Chem 14:3467

    Article  CAS  Google Scholar 

  10. Lee SY, Kwak YH, Park Bw (2013) Us Pat. US 2013/0048955 A1

  11. Wang QY, Zhang ZT, Du ZC, Hua HL, Chen SS (2013) Green Chem 15:1048

    Article  Google Scholar 

  12. Sheldrick GM (1997) SHELX-97 program package for crystal structure solution and refinement. University of Gǒttingen, Germany

    Google Scholar 

  13. Janiak C (2000) J Chem Soc Dalton Trans 21:3885

    Article  Google Scholar 

Download references

Acknowledgements

The authors are thankful for financial support from the Talent Project of Weinan Noraml University (No.17ZRRC04) and Natural Science Foundation Program of Shaanxi Science and Technology Department (No. 2019JQ-902).

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Authors and Affiliations

  1. College of Chemistry and Materials, WeiNan Normal University, WeiNan, 714099, People’s Republic of China

    Qiu-Ya Wang

  2. School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, People’s Republic of China

    Zun-Ting Zhang

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  1. Qiu-Ya Wang
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  2. Zun-Ting Zhang
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Correspondence to Qiu-Ya Wang.

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10870_2020_835_MOESM1_ESM.doc

Electronic supplementary material 1 (DOC 434 kb) Supplementary Materials"CCDC-1948559 and 1948560 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk /conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)12 23-336033; email: deposit@ ccdc .cam.ac.uk]."

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Wang, QY., Zhang, ZT. Syntheses and Crystal Structures of Two 2H-dibenzo[e, g]indazoles. J Chem Crystallogr 51, 161–168 (2021). https://doi.org/10.1007/s10870-020-00835-4

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  • DOI: https://doi.org/10.1007/s10870-020-00835-4

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