Patent ID: 6268497
Filing Date: 2001-07-31
Classification: C07D

Abstract:
A process for the preparation of a compound of structural formula 3 ##STR10##wherein R.sup.1-6 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 (where 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 (where 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, optionally substituted ring), OR.sup.9 (where R.sup.9 represents 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), NR.sup.7 R.sup.9, SR.sup.9, SOR.sup.9, SO.sub.2 R.sup.9 ;R.sup.10-11 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.9 or Cl; R.sup.12-13 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, alternatively, R.sup.12-13 can combine to form a three- to eight-membered, optionally substituted ring;R.sup.14 represents C.sub.1 -C.sub.12 alkyl, substituted C.sub.1 -C.sub.6 alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, allyl, substituted allyl, olefin, substituted olefin, alkyne or substituted alkyne; that comprises the steps of:a) treating a lactol of structural formula 4 ##STR11##with an optionally substituted 1,2-diol or 1,2-diol monoether of structural formula 10 ##STR12##in the presence of a catalyst, in a first inert solvent to form a compound of structural formula 8 ##STR13##wherein R.sup.15-17 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; R.sup.18 represents H, C.sub.1 -C.sub.6 alkyl, benzyl or substituted benzyl; or, alternatively, any two of R.sup.15-18 may combine to form a four- to seven-membered, optionally substituted ring; andb) treating the mixed acetal 8 with an organomagnesium halide (Grignard reagent) in a second inert solvent to form a chromenoquinoline of structural formula 3.