One-pot synthesis of 2-substituted 4-aryl-4,5-dihydro-3,1-benzoxazepines from 2-(2-Aminophenyl)-1-arylethanols via dehydration of the corresponding amides

Helvetica Chimica Acta

Volumn 94, Issue 6, 2011, Pages 987-992

  Fukamachi, Shuhei ^a   Konishi, Hisatoshi ^a   Kobayashi, Kazuhiro ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

3,1 Benzoxazepines, 4,5 dihydro ; Dehydration; Ethanols, 2 (2 aminophenyl); Imino ethers, cyclic; Phosphoryl chloride

Indexed keywords

3,1-BENZOXAZEPINES, 4,5-DIHYDRO-; ACID CHLORIDES; EFFICIENT METHOD; IMINO ETHERS, CYCLIC; ONE-POT REACTION; ONE-POT SYNTHESIS; PHOSPHORYL CHLORIDE; ROOM TEMPERATURE;

AMIDES; CHLORINE COMPOUNDS; DEHYDRATION; DEWATERING; ETHERS; REACTION INTERMEDIATES;

SYNTHESIS (CHEMICAL);

2 (4 CHLOROPHENYL) 4,5 DIHYDRO 4 PHENYL 3,1 BENZOXAZEPINE; 2 (TERT BUTYL) 4,5 DIHYDRO 7 METHOXY 4 PHENYL 3,1 BENZOXAZEPINE; 2 ETHOXY 4,5 DIHYDRO 4 PHENYL 3,1 BENZOXAZEPINE; 2 ETHYL 4,5 DIHYDRO 4 PHENYL 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 2 (4 METHOXYPHENYL) 4 DIPHENYL 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 2,4 DIPHENYL 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 4 (3 METHOXYPHENYL) 2 PHENYL 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 4 PHENYL 2 (2 PHENYLETHENYL) 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 4 PHENYL 2 (PYRIDIN 3 YL) 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 4 PHENYL 2 (TRICHLOROMETHYL) 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 7 METHOXY 2 (1 METHYLETHYL) 4 PHENYL 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 7 METHOXY 4 PHENYL 2 (THIOPHEN 2 YL) 3,1 BENZOXAZEPINE; 4,5 DIHYDRO 7 METHOXY N,4 DIPHENYL 3,1 BENZOXAZEPINE; 8 CHLORO 4 (4 CHLOROPHENYL) 2 ETHYL 4,5 DIHYDRO 2 PHENYL 3,1 BENZOXAZEPINE; 8 CHLORO 4 (4 CHLOROPHENYL) 4,5 DIHYDRO 2 PHENYL 3,1 BENZOXAZEPINE; ALCOHOL DERIVATIVE; CHLORIDE; DIBENZOXAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 79959209754     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000421     Document Type: Article

References (9)

1. E. R. Kurbatov, A. V. Kurochkin, L. M. Korkodinova, B. Y. Syropyatov, L. N. Markova, Pharm. Chem. J. 2008, 42, 674
2. K. R. Shreder, J. Cajica, L. Du, A. Fraser, Y. Hu, Y. Kohno, E. C. K. Lin, S. J. Liu, E. Okerberg, L. Pham, J. Wu, J. W. Kozarich, Bioorg. Med. Chem. Lett. 2009, 19, 4743
3. B. D. Sanders, B. Jackson, M. Brent, A. M. Taylor, W. Dang, S. L. Berger, S. L. Schreiber, K. Howitz, R. Marmorstein, Bioorg. Med. Chem. 2009, 17, 7031
4. J. R. Miller, V. Thanabal, M. M. Melnick, M. Lall, C. Donovan, R. W. Sarver, D.-Y. Lee, J. Ohren, D. Emerson, Chem. Biol. Drug Des. 2010, 75, 444
5. P.-W. Hsieh, H.-P. Yu, Y.-J. Chang, T.-L. Hwang, Eur. J. Med. Chem. 2010, 45, 3111.
6. Y. Ito, K. Kobayashi, T. Saegusa, Tetrahedron Lett. 1978, 19, 2087
7. G. Capozzi, R. Ottana, G. Romeo, Heterocycles 1987, 26, 39
8. M. D. Ganton, M. A. Kerr, Org. Lett. 2005, 7, 4777.
9. T. Izumi, T. Yokota, J. Heterocyclic Chem. 1992, 29, 1085.