Heterocyclic compounds
Described herein are methods for synthesizing heterocyclic, 8-membered ring structures. The methods may allow for preparation of highly substituted 8-membered rings. Also disclosed are heterocyclic, 8-membered ring compounds and pharmaceutical compositions comprising the compounds.
1. A compound of formula (I):
wherein:
X is selected from the group consisting of O and NR 1 ;
R 1 is selected from the group consisting of hydrogen and a nitrogen protecting group;
R 2 is selected from the group consisting of —C(O)O—, —C(O)—, —O—, —NR 4 — and —CR 5 2 —;
each R 3 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, heteroaryl and cyano, any of which is optionally substituted;
R 4 is selected from the group consisting of hydrogen, alkyl, and a nitrogen protecting group; and
each R 5 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, acyl, alkoxy, amido, amino, carboxy, cyano, ester, halo, haloalkyl, hydroxy, nitro, phosphonate, sulfinyl, sulfonyl, sulfonate, sulfonamino and sulfonamido, any of which is optionally substituted; or two R 5 are taken together with the atom to which they are attached to form an optionally substituted ring system.
2. A pharmaceutical composition comprising a compound according to claim 1 .
3. The compound of claim 1 , wherein the nitrogen protecting group is an alkyl.