Skip to main content
Log in

Metallic magnesium: an efficient catalyst toward N-aryl and N-alkyl substituted amides directly from aliphatic carboxylic acids

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An efficient and inexpensive procedure for direct conversion of aliphatic carboxylic acids into amides has been developed using anilines or aliphatic amines and Mg(0) as catalyst in toluene. The amides were obtained by single crystallization in moderate to excellent yields with high purity.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1

Similar content being viewed by others

References

  1. Yehia AH, Bialer M (1990) J Pharm Sci 79:719

    Article  Google Scholar 

  2. Alvarado M, Goya P, Gonzalez MM, Pavon FJ, Serrano A, Jagerovic N, Elguero J, Rodriguez AG, Granda SG, Suaridaz M, De Fonseca FR (2008) Bioorg Med Chem 16:10098

    Article  CAS  Google Scholar 

  3. De Petrocellis L, Melck D, Bisogno T, Di Marzo V (2000) Chem Phys Lipids 108:191

    Article  Google Scholar 

  4. Da Ros Montes D’Oca C, Coelho T, Marinho TG, Hack CRL, Da Costa Duarte R, Da Silva PA, Montes D’Oca MG (2010) Bioorg Med Chem Lett 20:5255

  5. Almeida B, Joglar J, Rojas MJL, Decara JM, Silva FJB, Gonzalez MM, Fito M, Cuevas MR, Farre M, Covas MI, De Fonseca FR, De la Torre R (2010) ChemMedChem 5:1781

    Article  CAS  Google Scholar 

  6. Dang HT, Kang GJ, Yoo ES, Hong J, Choi JS, Kim HS, Chung HY, Jung JH (2011) Bioorg Med Chem 19:1520

    Article  CAS  Google Scholar 

  7. Magne FC, Mod RR, Sumrell G (1974) J Am Oil Chem Soc 51:93

    Article  Google Scholar 

  8. Yıldırım A, Öztürk S, Çetin M (2013) J Surfact Deterg 16:13

    Article  Google Scholar 

  9. Öztürk S, Yıldırım A, Çetin M, Tavaslı M (2014) J Surfact Deterg 17:471

    Article  Google Scholar 

  10. Bower S, Kreutzer KA, Buchwald SL (1996) Angew Chem Int Ed 35:13

    Article  Google Scholar 

  11. Ruck RT, Bergman RG (2004) Angew Chem Int Ed 43:5375

    Article  Google Scholar 

  12. Li LC, Ren J, Liao TG, Jiang JX, Zhu HJ (2007) Eur J Org Chem 1026

  13. Kuo CW, Zhu JL, Wu JD, Chu CM, Yao CF, Shia KS (2007) Chem Commun 3:301

    Article  Google Scholar 

  14. Raja EK, DeShepper DJ, Lill SON, Klumpp DA (2012) J Org Chem 77:5788

    Article  CAS  Google Scholar 

  15. Bistline RG, Maurer EW, Smith FD, Linfield WM (1980) J Am Oil Chem Soc 57:98

    Article  CAS  Google Scholar 

  16. Cvetovich RJ, DiMichele L (2006) Org Process Res Dev 10:944

    Article  CAS  Google Scholar 

  17. Narasimhan B, Narang R, Judge V, Ohlan R, Ohlan S (2007) Arkivoc xv:112

  18. Buijnsters PJJA, Rodriguez CLG, Willighagen EL, Sommerdijk NAJM, Kremer A, Camilleri P, Feiters MC, Nolte RJM, Zwanenburg B (2002) Eur J Org Chem 1397

  19. Yao LY, Lin Q, Niu YY, Deng KM, Zhang JH, Lu Y (2009) Molecules 14:4051

    Article  CAS  Google Scholar 

  20. Ge YS, Tai SH, Xu ZQ, Lai L, Tian FF, Li DW, Jiang FL, Liu Y, Gao ZN (2012) Langmuir 28:5913

    Article  CAS  Google Scholar 

  21. Duan SY, Ge XM, Lu N, Wu F, Yuan W, Jin T (2012) Int J Nanomed 7:3813

    CAS  Google Scholar 

  22. Srinivas KVNS, Das B (2003) J Org Chem 68:1165

    Article  CAS  Google Scholar 

  23. Yang XD, Zeng XH, Zhao YH, Wang XQ, Pan ZQ, Li L, Zhang HB (2010) J Comb Chem 12:307

    Article  CAS  Google Scholar 

  24. Komura K, Nakano Y, Koketsu M (2011) Green Chem 13:828

    Article  CAS  Google Scholar 

  25. Nezhad AK, Zare A, Parhami A (2007) Phosphorus Sulfur Silicon Relat Elem 182:657

    Article  Google Scholar 

  26. Nezhad AK, Parhami A, Rad MNS, Zarea A (2005) Tetrahedron Lett 46:6879

    Article  Google Scholar 

  27. Starkov P, Sheppard TD (2011) Org Biomol Chem 9:1320

    Article  CAS  Google Scholar 

  28. Lanigan RM, Starkov P, Sheppard TD (2013) J Org Chem 78:4512

    Article  CAS  Google Scholar 

  29. Khazaei A, Mallakpour S, Zolfigol MA, Vaghei RG, Kolvari E (2004) Phosphorus Sulfur Silicon Relat Elem 179:1715

    Article  CAS  Google Scholar 

  30. Menezes FG, Kolling R, Bortoluzzi AJ, Gallardo H, Zucco C (2009) Tetrahedron Lett 50:2559

    Article  CAS  Google Scholar 

  31. Kawagoe Y, Moriyama K, Togo H (2013) Tetrahedron 69:3971

    Article  CAS  Google Scholar 

  32. White JM, Tunoori AR, Turunen BJ, Georg GI (2004) J Org Chem 69:2573

    Article  CAS  Google Scholar 

  33. Kangani CO, Kelley DE (2005) Tetrahedron Lett 46:8917

    Article  CAS  Google Scholar 

  34. Gertzmann R, Gürtler C (2005) Tetrahedron Lett 46:6659

    Article  CAS  Google Scholar 

  35. Nezhad AK, Mokhtari B, Rad MNS (2003) Tetrahedron Lett 44:7325

    Article  Google Scholar 

  36. Han KJ, Tae BS, Kim M (2005) Org Prep Proced Int 37:198

    Article  CAS  Google Scholar 

  37. Zhang Z, Yu Y, Liebeskind LS (2008) Org Lett 10:3005

    Article  CAS  Google Scholar 

  38. Terada Y, Ieda N, Komura K, Sugi Y (2008) Synthesis 2318

  39. McNulty J, Krishnamoorthy V, Robertson A (2008) Tetrahedron Lett 49:6344

    Article  CAS  Google Scholar 

  40. Chaudhari PS, Salim SD, Sawant RV, Akamanchi KG (2012) Green Chem 12:1707

    Article  Google Scholar 

  41. Tamaddon F, Aboee F, Nasiri A (2011) Catal Commun 16:194

    Article  CAS  Google Scholar 

  42. Lee KS, Kim KD (2011) Synth Commun 41:3497

    Article  CAS  Google Scholar 

  43. Gernigon N, Al-Zoubi RM, Hall DG (2012) J Org Chem 77:8386

    Article  CAS  Google Scholar 

  44. Lundberg H, Tinnis F, Adolfsson H (2012) Synlett 23:2201

    Article  CAS  Google Scholar 

  45. Bahrami K, Khodaei MM, Targhan N, Arabi MS (2013) Tetrahedron Lett 54:5064

    Article  CAS  Google Scholar 

  46. Huang L, Guo H, Pan L, Xie C (2013) Eur J Org Chem 6027

  47. Kumar PS, Kumar GS, Kumar RA, Reddy NV, Reddy KR (2013) Eur J Org Chem 1218

  48. Bai J, Zambron BK, Vogel P (2014) Org Lett 16:604

    Article  CAS  Google Scholar 

  49. Sarvari MH, Sodagar E, Doroodmand MM (2011) J Org Chem 76:2853

    Article  Google Scholar 

  50. De Jonge AP, Van Der Van B, Hertog WD (1956) Recl Trav Chim Pays-Bas 75:5

    Article  Google Scholar 

  51. Jursic BS, Zdravkovski V (1993) Synth Commun 23:2761

    Article  CAS  Google Scholar 

  52. Hodgson HH, Marsden E (1937) J Chem Soc 1365

  53. Grimmel HW, Guenther A, Morgan JF (1946) J Am Chem Soc 68:539

    Article  CAS  Google Scholar 

  54. Stamatovska V, Dimova V, Ragenovik KC (2006) Bull Chem Technol Maced 25:9

    CAS  Google Scholar 

  55. Mali SM, Bhaisare RD, Gopi HN (2013) J Org Chem 78:5550

    Article  CAS  Google Scholar 

  56. Thalluri K, Nadimpally KC, Paul A, Mandal B (2012) RSC Adv 2:6838

    Article  CAS  Google Scholar 

  57. Perry NB, Burgess EJ, Lorimer SD, Van Klink JW (1996) Phytochem Anal 7:263

    Article  CAS  Google Scholar 

  58. Gooßen LJ, Ohlmann DM, Lange PP (2009) Synthesis 160

  59. Terada Y, Ieda N, Komura K, Sugi Y (2008) Synthesis 2318

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ayhan Yıldırım.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 8816 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yıldırım, A. Metallic magnesium: an efficient catalyst toward N-aryl and N-alkyl substituted amides directly from aliphatic carboxylic acids. Monatsh Chem 146, 947–951 (2015). https://doi.org/10.1007/s00706-014-1387-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1387-2

Keywords

Navigation