Ammonium salts as convenient ammonia surrogates in the willgerodt reaction

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

A novel solventless modification of the Willgerodt reaction is proposed. It employs elemental sulfur and ammonium salts as safe and convenient surrogates of ammonia on a solid carrier. The reaction involving combination of ammonium carbonate and aluminum oxide results in the amides of aryl acetic acids with yields from 48 to 85%.

全文:

受限制的访问

作者简介

E. Kvetkin

Samara State Medical University

编辑信件的主要联系方式.
Email: eakvetkin@gmail.com
ORCID iD: 0009-0009-1014-0297
俄罗斯联邦, Chapayevskaya St., 89, Samara, 443099

A. Sokolov

Samara State Medical University

Email: eakvetkin@gmail.com
ORCID iD: 0000-0003-4965-3136
俄罗斯联邦, Chapayevskaya St., 89, Samara, 443099

参考

  1. Yang L., Zhang M., Liu Q., Wei K., Chen Z., Xu W., J. Saudi Chem. Soc., 2021, 25, 101389. doi: 10.1016/j.jscs.2021.101389
  2. Vujjini S.K., Datla V.R.K.R., Badarla K.R., Vetukuri V.N.K.V.P.R., Bandichhor R., Kagga M., Cherukupally P., Tetrahedron Lett., 2014, 55, 3885–3887. doi: 10.1016/j.tetlet.2014.03.106
  3. Du S., Lu H., Yang D., Li H., Gu X., Wan C., Jia C., Wang M., Li X., Qiu Z., Molecules, 2015, 20, 4071–4087. doi: 10.3390/molecules20034071
  4. Du X.-J., Bian Q., Wang H.-X., Yu S.-J., Kou J.-J., Wang Z.-P., Li Z.-M., Zhao G., Org. Biomol. Chem., 2014, 12, 5427–5434. doi: 10.1039/c4ob00744a
  5. Willgerodt C. Ber. Dtsch. Chem. Ges., 1887, 20, 2467–2470. doi: 10.1002/cber. 18870200278
  6. Carmack M., Spielman M.A. Org. react., 1946, 3, 83–107. doi: 10.1002/0471264180.or003.02
  7. Sato R. Ammonium Sulfide. In: Encyclopedia of Reagents for Organic Synthesis, New York: Wiley, 2001. doi: 10.1002/047084289X.ra097
  8. DeTar D.F., Carmack M. J. Am. Chem. Soc., 1946, 68, 2025–2029. doi: 10.1021/ja01214a047
  9. Naidu P.P., Raghunadh A., Rao K.R., Mekala R., Babu J.M., Rao B.R., Siddaiah V., Pal M. Synth. Commun. 2014, 44, 1475–1482. doi: 10.1080/00397911.2013.862551
  10. Urbiña-Alvarez J., Rincón-Carvajal S., Gamba-Sán-chez D. Org Biomol Chem., 2023, 21, 7036–7051. doi: 10.1039/D3OB01202F
  11. Han W., Chen Y.-L., Tang X., Zhou J., Ma M., Shen Z.-L., Chu X.-Q. Green Chem., 2023, 25, 9672–9679. doi: 10.1039/D3GC03717G
  12. Chaurasia S.R., Bhanage B.M. Mol. Catal., 2020, 492, 110998. doi: 10.1016/j.mcat.2020.110998
  13. Sokolov A.V., Kvetkin E.A. New J. Chem., 2024, 48, 12444. doi: 10.1039/D4NJ01335B
  14. Rezaei M., Amani K., Darvishi K. Catal. Commun., 2017, 91, 38–42. doi: 10.1016/j.catcom.2016.12.004
  15. Deng L., Chen L., Zhu L., Li Y., Ou-Yang J., Wu S., Chen P., Shen S., Guo J., Zhou Y., Au C.-T., Yin S.-F. Chem. Eng. Sci., 2022, 261, 117960. doi: 10.1016/j.ces.2022.117960
  16. Priebbenow D.L., Bolm C. Chem. Soc. Rev., 2013, 42, 7870–7880. doi: 10.1039/c3cs60154d
  17. Пономарёва Т.Н., Елисеенков Е.В., Петров А.А., Боярский В.П. ЖОрХ. 2020, 56, 726–734. [Ponomareva T.N., Eliseenkov E.V., Petrov A.A., Boyarskii V.P. Russ. J. Org. Chem., 2020, 56, 781–787.] doi: 10.1134/S1070428020050097
  18. Radfar I., Abbasi S., Miraki M.K., Yazdani E., Karimi M., Heydari A. Chem. Select, 2018, 3, 3265–3267. doi: 10.1002/slct.201702906
  19. Rekunge D.S., Khatri C.K., Chaturbhuj G.U. Monatshefte Für Chem. – Chem. Mon., 2017, 148, 2091–2095. doi: 10.1007/s00706-017-2013-x
  20. Lundstedt T., Thorén P., Carlson R., Norin T., Mörch L. Acta Chem. Scand., 1984, 38b, 717–719. doi: 10.3891/acta.chem.scand.38b-0717
  21. Bader H., Allen R.H., McCarty F.J. J. Org. Chem., 1966, 31, 2319–2391. doi: 10.1021/jo01345a056
  22. Yi Z., Huang M., Wan Y., Zhu X. Synthesis, 2018, 50, 3911–3920. doi: 10.1055/s-0037-1609578
  23. Veisi H., Maleki B., Hamelian M., Ashrafi S.S. RSC Adv., 2015, 5, 6365–6371. doi: 10.1039/c4ra09864a
  24. Wenner W. J. Org. Chem., 1950, 15, 548–551. doi: 10.1021/jo01149a016
  25. Carney R.W.J., De Stevens G. Пат. DE 1913743 A1 (1969). ФРГ.
  26. Miwatashi S., Arikawa Y., Naruo K., Igaki K., Watanabe Y., Kimura H., Kawamoto T., Ohkawa S. Chem. Pharm. Bull., 2005, 53, 410–418. doi: 10.1248/cpb.53.410
  27. Ohmura R., Takahata M., Togo H. Tetrahedron Lett., 2010, 51, 4378–4381. doi: 10.1016/j.tetlet.2010.06.05

补充文件

附件文件
动作
1. JATS XML
下载
2. Scheme

下载 (215KB)
索引源数据
3. Figure: Yields of the Wilgerodt reaction products

下载 (165KB)
索引源数据
4. Figure

下载 (108KB)
索引源数据

版权所有 © Russian Academy of Sciences, 2025