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Details for Patent: 4,036,842

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Details for Patent: 4,036,842

Title: Process for preparing polycyclic heterocycles having a pyran ring
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-l-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. (Montreal, CA), Jirkovsky; Ivo L. (Montreal, CA)
Assignee: American Home Products Corporation (New York, NY)
Filing Date:Sep 15, 1975
Application Number:05/613,160
Claims:1. A process for preparing a polyclclic heterocycle compound having a pyran ring which comprises reacting in the presence of a Friedel Crafts type catalyst a compound of the formula II:

wherein B is ##STR80## with a compound of the formula III: ##STR81## in which L and M each represent lower alkoxy or together represent the ethylenedioxy radical or oxo, and wherein R.sup.1 is hydrogen, lower alkyl, phenyl or p-halophenyl, and R.sup.2 is 2-furyl, 2-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl; or R.sup.2 is ##STR82## wherein R.sup.7 and R.sup.8 are the same or different and each represent halo, hydroxyl, carboxyl, carb(lower)alkoxy, or R.sup.1 and R.sup.2 together with the carbon atoms to which they are both joined to form a radical of the formula ##STR83## in which R.sup.6 is lower alkyl.

2. The process of claim 1 wherein said catalyst is selected from the group consisting of p-toluenesulfonic acid, phosphorus pentoxide, boron trifluoride, zinc chloride, hydrochloric acid or sulfuric acid.

3. The process of claim 1 wherein said catalyst is hydrogen chloride.

4. The process of claim 1 wherein the compound of formula 11 is reacted with the compound of formula 111 for a period of from about 10 minutes to about 60 hours, at a temperature ranging from about -20.degree. C. to the boiling point of the reaction mixture, and employing from about 0.01 to about 100 molar equivalents of the Friedel Crafts reaction catalyst.

5. The process of claim 1 wherein the compound of formula 11 is reacted with the compound of formula 111 for a period of from about 10 minutes to about 60 hours, at a temperature ranging from about 20.degree. C. to the boiling point of the reaction mixture, and employing from about 0.01 to about 100 molar equivalents of the Friedel-Crafts reaction catalyst.

6. The process of claim 5 wherein B is ##STR84## R.sup.1 and R.sup.2 together with the carbon atom to which they are both joined form a radical of the formula ##STR85## L and M together represent oxo, and the component of formula 111 is ethyl 2-cyclohexanone acetate.

7. The process of claim 5 wherein B is ##STR86## R.sup.1 and R.sup.2 together with the carbon atom to which they are both joined form a radical of the formula ##STR87## L and M together represent oxo, and the compound of formula III is ethyl 2-cyclopentanone carboxylate.

8. The process of claim 5 wherein B is ##STR88## R.sup.1 and R.sup.2 together with the carbon atom to whch they are both joined form a radical of the formula ##STR89## and the compound of formula III is 1-methyl-4-piperidone.

9. A process for preparing a polyclyclic heterocycle compound having a pyran ring which comprises reacting in the presence of a Friedel Crafts type catylyst a compound of the formula II:

wherein B is ##STR90## with a compound of the formula III: ##STR91## in which R.sup.1 is n--C.sub.3 H.sub.7,R.sup.2 is CH.sub.2 COOC.sub.2 H.sub.5, and L and M taken together are oxo.

10. A process for preparing a polycyclic heterocycle compound having a pyran ring which comprises reacting in the presence of a Friedel Crafts type catylyst a compound of the formula II:

wherein B is ##STR92## with a commpound of the formula III: ##STR93## in which R.sup.1 is CH.sub.3, or n--C.sub.3 H.sub.7 ; R.sub.2 is CH.sub.2 COOC.sub.2 H.sub.5, and L and M taken together are oxo.

11. A process for preparing 1-acetyl-4',9'-dihydrospiro[piperidine-4,1'-(3'H)-pyrano[3,4-b]indole] which comprises reacting in the presence of a Friedel Crafts type catalyst a compound of the formula II:

wherein B is ##STR94## with 1-acetyl-4-piperidone.
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