Patent ID: 6180794
Filing Date: 2001-01-30
Classification: C07D

Abstract:
A process for the preparation of a 1,2-dihydroquinoline of structural formula 15, ##STR12##wherein R.sup.16-17 independently represent H, C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl, allyl, substituted allyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, OR.sup.14 or Cl; or where R.sup.16 and R.sup.17 taken together form a five- to seven-membered, optionally substituted ring;R.sup.18-19 independently represent C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl, allyl, substituted allyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl; or where R.sup.18 and R.sup.19 taken together form a three-to eight-membered (preferably five-to eight-membered), optionally substituted ring;R.sup.20-23 independently represent H, C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl, F, Cl, Br, I, CN, CF.sub.3, CF.sub.2 CF.sub.3, CO.sub.2 R.sup.7 (wherein R.sup.7 represents H, C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl, allyl, substituted allyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl), CONR.sup.7 R.sup.8 (wherein R.sup.8 represents H, C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl, allyl, substituted allyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl; or where, alternatively, R.sup.7 and R.sup.8 combine to form a four-to seven-membered ring), allyl, substituted ally, aryl, substituted aryl, heteroaryl or substituted heteroaryl; or where R.sup.20 and R.sup.21 OR R.sup.21 and R.sup.22 OR R.sup.22 and R.sup.23 taken together form a five-to seven-membered ring;that comprises the steps of:a) treating an optionally substituted aniline with a halogenating agent to form an ortho-haloaniline; ##STR13##b) treating the ortho-haloaniline with a metallated olefin in the presence of a catalyst or catalysts to form an ortho-alkenylaniline of structure 14; ##STR14##andc) treating the ortho-alkenylaniline with a ketone in the presence of a catalyst to form a compound of structural formula 15.