|Abstract:||A process applicable to the preparation of a wide variety of novel polycyclic heterocycles having a newly-formed pyran ring is disclosed. According to the process an aromatic nucleus bearing an ethanol group, for example, 3,4-dimethoxyphenethyl alcohol, is condensed with an aldehyde or ketone or a protected aldehyde or ketone, for example, aminoactaldehyde diethyl acetal, in the presence of an acid catalyst to afford the polycyclic heterocycle, for example, 6,7-dimethoxy-1-isochromanmethylamine. The new heterocycles so formed are useful for preparing derivatives having antiinflammatory, antibacterial or antifungal activities.|
|Inventor(s):|| Dobson; Thomas A. (Dollard des Ormeaux, CA), Humber; Leslie G. (Dollard des Ormeaux, CA), Demerson; Christopher A. (St. Laurent, CA), Jirkovsky; Ivo L. (Montreal, CA) |
|Assignee:|| American Home Products Corp. (New York, NY) |
|Filing Date:||Jan 07, 1980|
|Claims:||1. A compound of formula 1 ##STR27## wherein R.sup.3 and R.sup.4 each are hydrogen, hydroxyl or lower alkoxy; R.sup.1 is hydrogen, or lower alkyl; and R.sup.2 is 2-thienyl, 2-pyridyl, 3-pyridyl or ##STR28## wherein R.sup.7 and R.sup.8 are the same or different and each represent hydrogen, halo, or hydroxyl with the proviso that when R.sup.7 and R.sup.8 are hydrogen, then R.sup.3 and R.sup.4 are hydroxyl, and when R.sup.7 or R.sup.8 is halo then R.sup.3 and R.sup.4 is hydroxyl or lower alkoxy. |
2. 1-(4-Chlorophenyl)-6,7-dimethoxyisochroman, as claimed in claim 1.
3. 1-(2,6-Dichlorophenyl)-6,7-dimethoxyisochroman, as claimed in claim 1.
4. m-(6,7-Dimethoxyisochroman-1-yl)phenol, as claimed in claim 1.
5. 6,7-Dimethoxy-1-(2-thienyl)isochroman, as claimed in claim 1.
6. 6,7-Dimethoxy-1-(3-pyridyl)isochroman, as claimed in claim 1.
7. 6,7-Dimethoxy-1-(2-pyridyl)isochroman, as claimed in claim 1.
8. 1-(2-Thienyl)-6-isochromanol, as claimed in claim 1.