Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York A New Synthesis of 2-Benzazepines Alan R. Katritzky*, Rexiat Maimait, Yong-Jiang Xu, Rena G. AkhmedovaCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USAFax: +1(352)3929551; e-Mail: katritzky@chem.ufl.edu; Recommend Article Abstract Buy Article All articles of this category Abstract AlCl3-mediated intramolecular cyclization of N,N-bis(1H-1,2,3-benzotriazol-1-ylmethyl)-3-phenyl-1-propanamine (5) gave 2-benzotriazolylmethyl-2,3,4,5-tetrahydro-1H-2-benzazepine (6). Subsequent nucleophilic substitution of the benzotriazolyl group in 6 with Grignard reagents, triethyl phosphite and sodium borohydride afforded 2,3,4,5-tetrahydro-1H-2-benzazepines 1a-e, 2 and 3. Similarly, TiCl4-mediated cyclization of 8 and 10 gave 5,6,7,13b-tetrahydro-9H-isoindolo[1,2-a][2]benzazepin-9-one (9) and 1,2,5,6,7,11b-hexahydro-3H-pyrrolo[2,1-a][2]benzazepin-3-one (11), respectively. Key words benzotriazole - 2-benzazepine - cyclization - synthesis Full Text References References 1 Kasparek S. In Advances in Heterocyclic Chemistry Katritzky AR. Boulton AJ. Academic Press; New York: 1974. p.45 2a Fuller RW. Molloy BB. Hemrick SK. Biochem. Pharmacol. 1979, 28: 528 2b Trybulski EJ. Benjamin L. Vitone S. Walser A. Fryer RI. J. Med. Chem. 1983, 26: 367 2c Trybulski EJ. Fryer RI. Reeder E. Walser A. Blount J. J. Med. Chem. 1983, 26: 1596 3 Deady LW. Pirzada NH. Topsom RD. J. Chem. Soc., Perkin Trans 1 1973, 782 4 Orazi OO. Corral RA. Giaccio H. J. Chem. Soc., Perkin Trans. 1 1986, 1977 5 Grunewald GL. Paradkar VM. Stillions DM. Ching F. J. Heterocycl. Chem. 1991, 28: 1587 6 Jensen BL. Chockalingam K. J. Heterocycl. Chem. 1986, 23: 343 7 Molloy BB. inventors; Canadian Patent 1/119/592. ; Chem. Abstr. 1982, 97, 388632 8 Grunewald GL. Dahanukar VH. Ching P. Criscione KR. J. Med. Chem. 1996, 39: 3539 9 Perchonock CD. Lantos I. Finkelstein JA. Holden KG. J. Org. Chem. 1980, 45: 1950 10 Katritzky AR. Xu Y.-J. He H.-Y. Mehta S. J. Org. Chem. 2001, 66: 5590 11 Katritzky AR. Lan X. Yang JZ. Denisko OV. Chem. Rev. 1998, 98: 409 12 Walker GN. Engle AR. Kempton RJ. J. Org. Chem. 1972, 37: 3755
