Skip to main content

Alkylation of NH-, OH-, and SH-acids in the presence of potassium carbonate

1. Functionalization of chloromethyl group of alkoxy-substituted aromatic aldehydes

Abstract

An easily scalable, economocal, and more safe method for the preparation of 3-chloromethyl-4-methoxybenzaldehyde was developed. The latter was subjected to reactions with NH-, OH-, and SH-acids in the presence of potassium carbonate to obtain new aromatic aldehydes in high yields.

This is a preview of subscription content, access via your institution.

References

  1. P. Rothemund, J. Am. Chem. Soc., 1935, 57, 2010.

    Article  CAS  Google Scholar 

  2. R. G. Little, J. Heterocycl. Chem., 1981, 18, 833.

    Article  CAS  Google Scholar 

  3. R. De Paula, M. A. F. Faustino, D. C. Pinto, M. G. Neves, J. A. S. Cavaleiro, J. Heterocycl. Chem., 2008, 45, 453.

    Article  CAS  Google Scholar 

  4. L. Maqueira, A. Iribarren, A. C. Valdés, C. P. de Melo, C. G. dos Santos, J. Porphyrins Phthalocyanines, 2012, 16, 267.

    Article  CAS  Google Scholar 

  5. W. M. Whaley, T. R. Govindachari, Org. React., 1951, 6, 151.

    Google Scholar 

  6. A. Couture, E. Deniau, P. Grandclaudon, S. Lebrun, Tetrahedron: Asymmetry, 2003, 14, 1309.

    Article  CAS  Google Scholar 

  7. J. M. Tinsley, Pictet—Spengler Isoquinoline Synthesis, in Name Reactions in Heterocyclic Chemistry, Eds J. J. Li, E. J. Corey, Wiley and Sons, Hoboken, 2005, 469.

  8. D. J. Mergott, S. J. Zuend, E. N. Jacobsen, Org. Lett., 2008, 10, 745.

    Article  CAS  Google Scholar 

  9. C. N. Eid, J. Shim, J. Bikker, M. Lin, J. Org. Chem., 2009, 74, 423.

    Article  CAS  Google Scholar 

  10. E. Awuah, A. Capretta, J. Org. Chem., 2010, 75, 5627.

    Article  CAS  Google Scholar 

  11. L.-Y. Zeng, C. Cai, J. Heterocycl. Chem., 2010, 47, 1035.

    Article  CAS  Google Scholar 

  12. A. Strakovsk, F. Avotins, M. Petrova, Rigas Tehniskas Universitates Zinatniskie Raksti, Serija 1: Materialzinatne un Lietiska Kimija, 2003, 6, 122.

    CAS  Google Scholar 

  13. X.-S. Wang, K. Yang, J. Zhou, S.-J. Tu, J. Comb. Chem., 2010, 12, 417.

    Article  CAS  Google Scholar 

  14. D. Shi, C. Shi, J. Wang, L. Rong, Q. Zhuang, X. Wang, J. Heterocycl. Chem., 2005, 42, 173.

    Article  CAS  Google Scholar 

  15. A. Gharib, B. R. H. Khorasani, M. Jahangir, M. Roshani, R. Safaee, Hindawi Publishing Corporation Organic Chemistry International, 2013, Article ID 848237.

    Google Scholar 

  16. K. Ramesh, K. Karnakar, G. Satish, B. S. P. Anil Kumar, Y. V. D. Nageswar, Tetrahedron Lett., 2012, 53, 69.

    Google Scholar 

  17. S. B. Bharate, N. Mupparapu, S. Manda, J. B. Bharate, R. Mudududdla, R. R. Yadav, R. A. Vishwakarma, ARKIVOC, 2012, 8, 308.

    Google Scholar 

  18. P. Biginelli, Ber., 1891, 24, 1317; 2962.

    Article  Google Scholar 

  19. H. E. Zaugg, W. B. Martin, Org. React., 1965, 14, 88.

    Google Scholar 

  20. J. Lu, H. Ma, Synlett, 2000, 63.

    Google Scholar 

  21. B. R. P. Kumar, G. Sankar, R. B. Nasir Baig, S. Chandrashekaran, Eur. J. Med. Chem., 2009, 44, 4192.

    Article  Google Scholar 

  22. A. Hantzsch, Ann., 1882, 215, 72.

    Google Scholar 

  23. P. Galatsis, Hantzsch Dihydro-Pyridine Synthesis, in Name Reactions in Heterocyclic Chemistry, Eds J. J. Li, E. J. Corey, Wiley and Sons, Hoboken, 2005, 304.

  24. R. Gupta, R. Gupta, S. Paul, A. Loupy, Synthesis, 2007, 18, 2835.

    Google Scholar 

  25. J. J. Vanden Eynde, A. Mayence, Molecules, 2003, 8, 381.

    Article  CAS  Google Scholar 

  26. L. N. Ferguson, Chem. Rev., 1946, 38, 227.

    Article  CAS  Google Scholar 

  27. W. Kantlehner, Eur. J. Org. Chem., 2003, 2530.

    Google Scholar 

  28. D. Grobelny, S. Witek, J. Prakt. Chem., 1980, 322, 536.

    Article  CAS  Google Scholar 

  29. Z.-L. Chen, W.-Q. Wan, J.-R. Chen, F. Zhao, D.-Y. Xu, Heterocycles, 1998, 48, 1739.

    Article  CAS  Google Scholar 

  30. A. McKillop, F. A. Madjdabadi, D. A. Long, Tetrahedron Lett., 1983, 24, 1933.

    Article  CAS  Google Scholar 

  31. R. S. Vardanyan, Sintez osnovnykh lekarstvennykh sredstv [Synthesis of Principal Medicines], MIA Publ., Moscow, 2004, 845 (in Russian).

    Google Scholar 

  32. N. M. Morlyan, D. S. Khachatryan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1978, 31(2), 866 (in Russian).

    CAS  Google Scholar 

  33. D. S. Khachatryan, N. M. Morlyan, R. G. Mirzoyan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1981, 34(8), 672 (in Russian).

    CAS  Google Scholar 

  34. D. S. Khachatryan, A. A. Vardapetyan, G. A. Panosyan, R. G. Mirzoyan, N. M. Morlyan, Zh. Org. Khim., 1990, 26, 2092

    CAS  Google Scholar 

  35. D. S. Khachatryan, J. Org. Chem. USSR (Engl. Transl.), 1990, 26].

    Google Scholar 

  36. D. S. Khachatryan, A. A. Vardapetyan, N. M. Morlyan, A. L. Razinov, K. R. Matevosyan, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 385

    Article  Google Scholar 

  37. D. S. Khachatryan, Izv. Akad. Nauk, Ser. Khim., 2015, 385].

    Google Scholar 

  38. K. Sanda, L. Rigal, M. Delmas, A. Gaset, Synthesis, 1992, 541.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. S. Khachatryan.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0395—0404, February, 2015.

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khachatryan, D.S., Razinov, A.L., Kolotaev, A.V. et al. Alkylation of NH-, OH-, and SH-acids in the presence of potassium carbonate. Russ Chem Bull 64, 395–404 (2015). https://doi.org/10.1007/s11172-015-0875-9

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0875-9

Keywords