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A novel approach to obtain 3-amino-1-benzothiophene-2-carbonitriles

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Chemistry of Heterocyclic Compounds Aims and scope

A simple one-step protocol for the synthesis of 3-amino-1-benzothiophene-2-carbonitriles from commercially or synthetically readily available S-(cyanomethyl) O-ethyl carbodithionate and 2-fluorobenzonitriles was developed.

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References

  1. Nagesh, H.; Padmashali, B.; Sandeep, C.; Yuvaraj, T. C. M.; Siddesh, M. B.; Mallikarjuna, S. M. Int. J. Pharm. Sci. Rev. Res. 2014, 28(2), 6.

    Google Scholar 

  2. Naganagowda, G.; Padmashali, B. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 1691.

    Article  CAS  Google Scholar 

  3. Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cara, C. L.; Preti, D.; Fruttarolo, F.; Pavani, M. G.; Tabrizi, M. A.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Balzarini, J.; Hadfield, J. A.; Brancale, A.; Hamel, E. J. Med. Chem. 2007, 50, 2273.

    Article  CAS  PubMed  Google Scholar 

  4. Pinto, E.; Queiroz, M. J. R. P.; Vale-Silva, L. A.; Oliveira, J. F.; Begouin, A.; Begouin, J. M.; Kirsch, G. Bioorg. Med. Chem. 2008, 16, 8172.

    Article  CAS  PubMed  Google Scholar 

  5. Khovidhunkit, W.; Shoback, D. M. Ann. Intern. Med. 1999, 130, 431.

    Article  CAS  PubMed  Google Scholar 

  6. Saravanan, G.; Alagarsamy, V.; Chinnasamy, A.; Prakash, R. Int. J. Pharm. Pharm. Sci. 2010, 2, 8386.

    Google Scholar 

  7. Keri, R. S.; Chand, K.; Budagumpi, S.; Balappa Somappa, S.; Patil, S. A.; Nagaraja, B. M. Eur. J. Med. Chem. 2017, 138, 1002.

    Article  CAS  PubMed  Google Scholar 

  8. Beck, J. R.; Yahner, J. A. J. Org. Chem. 1974, 39, 3440.

    Article  CAS  Google Scholar 

  9. Loidreau, Y.; Dubouilh-Benard, C.; Marchand, P.; Nourrisson, M.-R.; Duflos, M.; Buquet, C.; Corbière, C.; Besson, T. J. Heterocycl. Chem. 2013, 50, 1187.

    Article  CAS  Google Scholar 

  10. Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.-R.; Duflos, M.; Lozach, O.; Loaëc, N.; Meijer, L.; Besson, T. Eur. J. Med. Chem. 2012, 58, 171.

    Article  CAS  PubMed  Google Scholar 

  11. Carrington, D. E. L.; Clarke, K.; Scrowston, R. M. J. Chem. Soc. C 1971, 3903.

  12. Sokolov, A. I.; Mikhaylov, A. A.; Baleeva, N. S.; Baranov, M. S. Eur. J. Org. Chem. 2021, 4350.

  13. Tanaka, K.; Ono, N.; Kubo, Y.; Kaji, A. Synthesis 1979, 890.

  14. Abdellaoui, H.; Chen, X.; Xu, J. Synthesis 2017, 49, 2250.

    Article  CAS  Google Scholar 

  15. Huang, Z.; Xu, J. RSC Adv. 2013, 3, 15114.

    Article  CAS  Google Scholar 

  16. https://scifinder-n.cas.org/searchDetail/substance/655e066225b43e48fc8741ae/substanceSpectra

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The study was carried out with financial support from the Russian Science Foundation within the framework of scientific project No. 20-73-10195.

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Correspondence to Dmitry S. Ivanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2024, 60(1/2), 99–102

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Ivanov, D.S., Sokolov, A.I., Smirnov, A.Y. et al. A novel approach to obtain 3-amino-1-benzothiophene-2-carbonitriles. Chem Heterocycl Comp 60, 99–102 (2024). https://doi.org/10.1007/s10593-024-03299-y

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