Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones

Author:

Mahajan Sheena,Slathia Nancy,Kapoor Kamal K.ORCID

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference20 articles.

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2. A Multifunction Pd/Sc(OTf)3/Ionic Liquid Catalyst System for the Tandem One-Pot Conversion of Phenol to ε-Caprolactam

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4. In Advanced Organic Chemistry;Smith;John Wiley & Sons: New York,2001

5. For selected examples in liquid phase mediated by small organic molecules, see : (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272. (b) Chandrasekhar, S.; Gopalaiah, K. Tetrahedron Lett. 2003, 44, 755. (c) Furuya, Y.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 11240. (d) Zhu, M.; Cha, C.; Deng, W.-P.; Shi, X.-X. Tetrahedron Lett. 2006, 47, 4861. (e) Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2008, 73, 2894. (f) Pi, H.-J.; Dong, J.-D.; An, N.; Du, W.; Deng, W.- P. Tetrahedron 2009, 65, 7790. (g) Srivastava, V. P.; Patel, R.; Garima; Dhar, L.; Yadav, S. Chem. Commun. 2010, 46, 5808. (h) Yadav, L. D. S.; Patel, R.; Srivastava, V. P. Synthesis 2010, 11, 1771. (i) Augustine, J. K.; Kumar, R.; Bombrun, A.; Mandal, A. B. Tetrahedron Lett. 2011, 52, 1074. (j) Xu, F.; Wang, N.-G.; Tian, Y.-P.; Chen, Y.-M.; Liu, W.-C. Synth. Commun. 2012, 42, 3532. For selected examples using metallic Lewis acids, see: (k)Thakur, A.J.; Boruah, A.; Prajapati, D.; Sandhu, J.S. Synth. Commun. 2000, 30, 2105. (l) Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. (m) Yadav, J.S.; Reddy, B.V.S.; Madhavi, A.V.; Ganesha, Y.S.S. J. Chem. Res. Synop. 2002, 236. (n) De, S.K. Synth. Commun. 2004, 34, 3431. (o) Allen, C.L; Burel, C.; Williams J.M.J. Tetrahedron Lett. 2010, 51, 2724. (p) Sharma, S.K.; Bishopp, S.D.; Allen, C.L.; Lawrence, R.; Bamford, M.J.; Lapkin, A.A.; Plucinski, P.; Watson, R.J.; Williams, J.M.J. Tetrahedron Lett. 2011, 52, 4252. (q) Martinez-Asencio, A.; Yus, M.; Ramon, D.J. Tetrahedron Lett. 2012, 68, 3948. For selected examples in supercritical water, see : (r) Sato, O.; Ikushima, Y.; Yokoyama, T. J. Org. Chem. 1998, 63, 9100. (s) Ikushima, Y.; Hatakeda, K.; Sato, O.; Yokoyama, T.; Arai, M. Angew. Chem. Int. Ed. 1999, 38, 2910. (t) Ikushima, Y.; Hatakeda, K.; Sato, O.; Yokoyama, T.; Arai, M. J. Am. Chem. Soc. 2000, 122, 1908. (u) Boero, M.; Ikeshoji, T.; Liew, C.C.; Terakura, K.; Parrinello, M. J. Am. Chem. Soc. 2004, 126, 6280.

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