Synthesis of 1(3H)-imino-2-benzothiophene and 1-imino-1H-2-benzothiopyran derivatives by reactions of secondary o-(vinyl)thiobenzamide derivatives with iodine

Bulletin of the Chemical Society of Japan

Volumn 80, Issue 4, 2007, Pages 763-767

  Kobayashi, Kazuhiro ^a   Fujita, Seiki ^a   Hase, Masanori ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1(3H)-IMINO-2-BENZOTHIOPHENE; SODIUM HYDROGENCARBONATE;

ACETONITRILE; IODINE; REACTION KINETICS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

1 IMINO 1H 2 BENZOTHIOPYRAN; 1(3H) IMINO 2 BENZOTHIOPHENE; ACETONITRILE; BENZOTHIOPHENE DERIVATIVE; BICARBONATE; IODINE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; SYNTHESIS;

EID: 34247244183     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.763     Document Type: Article

References (7)

1. K. Kobayashi, M. Hase, K. Hashimoto, S. Fujita, M. Tanmatsu, O. Morikawa, H. Konishi, Synthesis 2006, 2493.
2. 3-Methyl(or Phenyl)-1-imino-3H-benzo[c]thiophenes have been prepared in low yields by a treatment of 2-(1-hydroxyalkyl)-benzamide derivatives with Lawesson's reagent: T. Nishio, H. Sekiguchi, Tetrahedron 1999, 55, 5017.
3. 3-Methyl-1-methylimino-2-benzothiopyran has been prepared in high yield by a reaction of a dianion, generated from 2,N-dimethylthiobenzamide, with acetyl chloride: D. Ach, V. Reboul, P. Metzner, Eur. J. Org. Chem. 2002, 2573.
4. M. E. Jason, Tetrahedron Lett. 1982, 23, 1635.
5. V. J. Bauer, B. J. Duffy, D. Hoffmann, S. S. Klioze, R. W. Kosely, Jr., A. R. McFadden, L. L. Martin, H. H. Ong, H. M. Geyer, III, J. Med. Chem. 1976, 19, 1315.
6. K. Kobayashi, T. Shiokawa, H. Omote, K. Hashimoto, O. Morikawa, H. Konishi, Bull. Chem. Soc. Jpn. 2006, 79, 1126.
7. I. Fleming, M. Woolias, J. Chem. Soc., Perkin Trans. 1 1979, 829.