Synthesis of chromanones
View Patent ↗Processes for the preparation of biologically active chromanones are disclosed, including processes for the preparation of intermediates useful in the preparation of the biologically active chromanones. The chromanones and the intermediates disclosed herein may be useful for a variety of therapies, including the treatment of various cancers and the treatment of inflammation and inflammation related disorders.
1. A chromanone corresponding to Formula 21:
wherein
R 5 is amino or nitro;
R 6 is amino, hydroxy, halo, perfluorinated sulfonic ester, R 61 C(O)—, R 62 C(O)O—, R 61 C(O)NH—, R 62 CHCH— or R 62 CC—;
R 21 and R 22 are independently hydrogen, alkyl, or aryl;
R 61 is hydrogen, heterocyclo, alkoxy, heterocyclooxy, amino, or halo, and
R 62 is hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclo, alkoxy, heterocyclooxy, amino, or halo.
2. The chromanone of claim 1 wherein R 5 is —NO 2 .
3. The chromanone of claim 1 wherein R 5 is —NH 2 .
4. The chromanone of claim 1 wherein R 6 is —OH.
5. The chromanone of claimi wherein R 6 is R 62 CHCH— or R 62 CC—.
6. The chromanone of claim 2 wherein R 6 is —OH.
7. The chromanone of claim 2 wherein R 6 is perfluorinated sulfonic ester.
8. The chromanone of claim 5 wherein R 5 is —NH 2 .
9. The chromanone of claim 8 wherein R 21 and R 22 are methyl.
10. The chromanone of claim 8 wherein R 62 is substituted hydrocarbyl.
11. A chromanone corresponding to Formula 62 or 67
wherein
R 62 is hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclo, alkoxy, heterocyclooxy, amino or halo; and
R 21 and R 22 are independently hydrogen, alkyl, or aryl.
12. The chromanone of claim 11 having the structure
13. The chromanone of claim 11 having the structure
14. The chromanone of claim 11 corresponding to Formula 62.
15. The chromanone of claim 11 corresponding to Formula 67.
16. The chromanone of claim 14 wherein R 62 is substituted alkyl and R 21 and R 22 are independently hydrogen or alkyl.
17. The chromanone of claim 15 wherein R 62 is substituted alkyl and R 21 and R 22 are independently hydrogen or alkyl.