An Efficient Synthesis of N-Cyclopropylanilines by a Smiles Rearrangement

Abstract

Treatment of 2-chloro-N-cyclopropylacetamide with phenols gave the corresponding 2-aryloxy-N-cyclopropylacetamides, which on treatment with a base gave the corresponding N-cyclopropylanilines.

Key words

rearrangements - amines - cyclopropanes

• References

• 1a Schriewer M, Petersen U, Grohe K, Krebs A. EP 0332033, 1989
• 1b Palomo Nicolau C, Cabre Castellvi F, Palomo Nicolau FE, Palomo Coll AL. EP 430847, 1991
• 1c Domingo Coto A, López Molina I, Palomo Coll A. ES 2015442, 1990
• 1d Freixas Bazaco J, Martorell Coca C. ES 2050613, 1994
• 1e Yoshida Y, Tabuchi F, Umetsu K, Hamada Y. JP11035530, 1999
• 1f Somfai E. WO 9502573, 1995
• 2 Cui W, Loeppky RN. Tetrahedron 2001; 57: 2953
• 3 Hanzlik RP, Kishore V, Tullman R. J. Med. Chem. 1979; 22: 759
• 4 Suckling J. Angew. Chem., Int. Ed. Engl. 1988; 27: 537
• 5 Salaun J. Russ. J. Org. Chem. (Engl. Transl.) 1997; 33: 742
• 6 Macdonald TL, Zirvi K, Burka LT, Peyman P, Guengerich FP. J. Am. Chem. Soc. 1982; 104: 2050
• 7 Zhao Z, Mabic S, Kuttab S, Franot C, Castagnoli K, Castagnoli NJr. Bioorg. Med. Chem. 1998; 6: 2531
• 8 Reichelt A, Martin FS. Acc. Chem. Res. 2006; 39: 433
• 9 Brown HC, Fletcher RS, Johannesen RB. J. Am. Chem. Soc. 1951; 43: 212
• 10 Bénard S, Neuville L, Zhu J. Chem. Commun. (Cambridge) 2010; 46: 3393
• 11a Kang J, Kim KS. J. Chem. Soc., Chem. Commun. 1987; 897
• 11b Yoshida Y, Umezu K, Hamada Y, Atsumi N, Tabuchi F. Synlett 2003; 2139
• 12 Gillaspy ML, Lefker BA, Hada WA, Hoover DJ. Tetrahedron Lett. 1995; 36: 7399
• 13 Noritaka K, Kazumasa N, Atsushi S, Atsushi K, Shinichi H, Tadashi O. US 2012004315, 2012