Download PDF
Synthesis 1997; 1997(1): 113-116
DOI: 10.1055/s-1997-1503
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Facile Synthesis of Substituted 5-11-Dihydro[1]benzoxepinol[3,4-b]pyridines

Kunimi Inoue1 , Toru Sugaya2 , Takehiro Ogasa2 , Shinji Tomioka3
  • 1Sakai Research Laboratories, Kyowa Hakko Kogyo Co., Ltd. 1-1-53 Takasu-cho, Sakai, Osaka 590, Japan, Fax +81(722)277214
  • 2Sakai Research Laboratories, Kyowa Hakko Kogyo Co., Ltd. 1-1-53 Takasu-cho, Sakai, Osaka 590, Japan
  • 3Yokkaichi Research Laboratories, Kyowa Hakko Kogyo Co., Ltd. 2-3 Daikyo-cho, Yokkaichi, Mie 510, Japan, Fax +81(593)333374
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

5-Amino-5,11-dihydro[1]benzoxepino[3,4-b]pyridines (1) show antiulcer and antiarrhythmic activity. An efficient method for the preparation of a key intermediate, furo[3,4-b]pyridin-5(7 H)-one (4), and the facile synthesis of 1 were described. The reduction of quinolinic anhydride (5) with sodium borohydride in the presence of acetic acid regioselectively gave the lactone 4. Lactone 4 was then reacted with substituted phenols under basic conditions and the resultant products, 2-(phenoxymethyl)-3-pyridinecarboxylic acids (3), underwent Friedel-Crafts cyclizations to produce the 5,11-dihydro[1]benzoxepino[3,4-b]pyridin-5-ones (2). Compounds 2 were then converted to imines with amines and successively reduced with zinc in acetic acid to the desired compounds 1.

quinolinic anhydride - regioselective reduction - azaphthalide Friedel-Crafts cyclization - 5,11-dihydro[1]benzoxepino-[3,4-b]pyridine

      >