A convenient synthesis of 2-benzazepines, which are attracting medicinal chemists due to their unique biological activity, is achieved by 7-endo selective radical cyclization of N-(o-bromobenzyl)methacrylamide. The mechanistic study on the radical cyclization revealed kinetic estimation of 7-endo cyclization. The intramolecular Friedel-Crafts reaction opens an alternative useful approach for these molecules. We have successfully prepared optically active 2-benzazepines and examined their biological activity. We have recently published kinetic analysis for the 7-endo selective radical cyclization.
Publications
Kamimura, A.; Taguchi, Y.; Omata, Y.; Hagihara, M. J. Org. Chem. 2003, 68, 4996-4998
Matsuura, K.; Kuratani, T.; Gondo, T.; Kamimura, A.; Inui, M. Eur. J. Pharmacol. 2007, 563, 83-87
Kamimura, A.; Ishihara, Y.; So, M.; Hayashi, T.; Tetrahedron Lett. 2009, 50, 1727-1730
Kamimura, A.; So, M.; Kuratani, T.; Matsuura, K.; Inui, M. Bioorg. Med.Chem. Lett. 2009, 19, 3193-3195
So, M.; Kotake, T.; Matsuura, K.; Inui, M.; Kamimura, A. J. Org. Chem. 2012, 77, 4017 – 4028.
Kamimura, A.; Kotake, T.; Ishihara, Y.; So, M.; Hayashi, T. J. Org. Chem. 2013, 78, 3961-3971, DOI:10.2021/jo400326b.
