Boron trifluoride etherate; highly efficient catalyst for synthesis of tert-butylamides via modified Ritter reaction in solvent free condition

الموضوعات : Journal of the Iranian Chemical Research

Masoud Mokhtary ¹ (Department of Chemistry, Rasht Branch, Islamic Azad University, PO Box 41325-3516, Rasht, IRAN)
Faranak Najafizadeh ² (Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, PO Box 678, Amol, IRAN)

تاريخ الإرسال : 05 الثلاثاء , ذو الحجة, 1432 تاريخ التأكيد : 02 الأحد , جمادى الأولى, 1433 تاريخ الإصدار : 27 الثلاثاء , ربيع الثاني, 1433

الکلمات المفتاحية: Modified Ritter reaction, Boron trifluoride etherate, Nitriles, tert-Butylacetate, N- tert- Butyl amides,

ملخص المقالة :

Highly efficient method for the preparation of N-tert-butyl amides by reaction of nitriles with tertbutylacetateis described using boron trifluoride etherate in solvent free condition. Selective amidation ofbenzonitrile in the presence of acetonitrile was also achieved.

المصادر:

[1] K. Tanaka. Solvent-free organic reaction,Wiley-VCH, Weinheim, 2003.
[2] J.J. Ritter, P.P. Paul, J. Am. Chem. Soc., 70 (1948) 4045-4048.
[3] H. Firozabadi, A.R. Sardarian, H. Badparva, Synth. Commun. 24 (1994) 601-607.
[4] M.M. Lakouraj, B. Movassagh, J. Fasihi, Synth. Commun. 30 (2000) 821-827.
[5] E. Callens, A.J. Burton, A.G.M. Barrett, Tetrahedron Lett. 47 (2006) 8699-8701.
[6] J.S. Yadav, B.V. Subba Reddy, G.G.K.S. Narayana Kumar, G.M. Reddy, Tetrahedron Lett. 48 (2007)
4903-4906.
[7] F. Tamaddon, M. Khoobi, E. Keshavarz, Tetrahedron Lett. 48 (2007) 3643-3646.
[8] V. Polshettiwar, R.S. Varma, Tetrahedron Lett. 49 (2008) 2661-2664.
[9] B.V. Subba Reddy, N. Sivasankar Reddy, Ch. Madan, J. S. Yadav, Tetrahedron Lett. 51 (2010) 4827–
4829.
[10] L.K. Reddy, Tetrahedron Lett. 44 (2003) 1453-1455.
[11] J.C. Baum, J.E. Milne, J.A. Murry, O.R. Thiel, J. Org. Chem. 74 (2009) 2207-2209.
[12] B. Anxionnat, A. Guérinot, S. Reymond, J. Cossy, Tetrahedron Lett. 50 (2009) 3470- 3473.
[13] F. Tamaddon, F. Tavakoli, J. Mol Catal A: Chem. 337 (2011) 52-55.
[14] P. Theerthagiri, A. Lalitha, P.N. Arunachalam, Tetrahedron Lett. 51 (2010) 2813-2819.
[15] M. Mokhtary, G. Goodarzi, Chin. Chem. Lett. 23 (2012) 293–296.
[16] H. Yamamoto, Lewis acid in organic synthesis, Wily-VCH, Weinheim, 2002.
[17] M.M. Lakouraj, M. Mokhtary, Polym. Int. 58 (2009) 1167-1172.
[18] M.M. Lakouraj, M. Mokhtary, J. Polym. Res. 16 (2009) 681-686.