Patent HU-0101104-A2 (HU)
Title: Process for preparing resorcinol derivatives
Inventor: BRADLEY STUART EDWARD
IPC: C07C37/00
Filed: 2001-03-14
Abstract: Preparation of 4-substituted resorcinol derivatives (I) or (II) comprises reacting 1-alkoxy or hydroxy-6-halo-3-substituted-2-oxabicyclo(2.2.2)octane-5-one (II) or 4-substituted-2-halo-cyclohexan-1,3-dione (III) with a base. Process (A) for the preparation of 4-substituted resorcinol derivatives of formulae (I) or (II) comprises reacting 1-alkoxy or hydroxy-6-halo-3-substituted-2-oxabicyclo(2.2.2)octane-5-one of formula (II) or 4-substituted-2-halo-cyclohexan-1,3-dione of formula (III) with a base. [Image] W : H or protecting group; X, Y : 1-12C alkyl, 2-12C alkenyl or 2-12C alkynyl (all optionally substituted by 1-3 Z) or H, or CXY : 4-8C cycloalkyl or 5-8C cycloalkenyl ring (both optionally substituted by Z), provided that the 4-8C cycloalkyl ring or 5-8C cycloalkenyl ring is not aromatic; Z : CN, halo, 1-6C alkyl, aryl, 2-9C heterocycloalkyl, 2-9C heteroaryl, aryl-(1-6C)alkyl, =O, =CHO(1-6C) alkyl, NH 2, OH, 1-6C alkoxy, aryl-(1-6C)alkoxy, 1-6C acyl, 1-6C alkylamino, aryl (1-6C) alkylamino, amino(1-6C) alkyl, 1-6C alkoxy-CO-NH-, 1-6C alkylamino-CO-, 2-6C alkenyl, 2-6C alkynyl, OH-(1-6C)alkyl, 1-6C alkoxy-(1-6C)alkyl, 1-6C acyloxy-(1-6C)alkyl, NO 2, cyano-(1-6C)alkyl, halo-(1-6C)alkyl, nitro(1-6C)alkyl, trifluoromethyl, trifluoromethyl-(1-6C)alkyl, 1-6C acylamino, (1-6C)acyl amino (1-6C)alkyl, 1-6C alkoxy-(1-6C)acylamino, amino(1-6C)acyl, amino-(1-6C)acyl-(1-6C)alkyl, 1-6C alkylamino-(1-6C)acyl, (1-6C alkyl) 2-amino(1-6C)acyl, -CO 2R 2>, 1-6C alkyl-CO 2R 2>, -C(O)N(R 2>) 2, 1-6C alkyl-C(O)N(R 2>) 2, R 2>ON=, R 2>ON=(1-6C)alkyl, R 2>ON=CR 2>(1-6C)alkyl, NR 2>(OR 2>), 1-6C alkyl-NR 2>(OR 2>), -C(O)(NR 2>OR 2>), 1-6C alkyl-C(O)(NR 2>OR 2>), S(O) mR 2>, R 3>C(O )O-, R 3>C(O)O-(1-6C)alkyl, R 4>R 5>N-C(O)O-, R 4>R 5>NS(O) 2, R 4>R 5>NS(O) 2 (1-6C)alkyl, R 4>S(O) 2R 5>N, R 4>S(O) 2R 5>N-(1-6C)alkyl, -C(=NR 6>)(N(R 4>) 2), -(1-6C)alkyl-C(=NR 6>)(N(R 4>) 2), -OC(O)aryl (1-6C)alkyl, NH(1-6C)alkyl, aryl-1-6C alkyl-HN or a ketal; R 3>1-6C alkyl, aryl or aryl-1-6C alkyl; R 2>H or R 3>; R 4>, R 5>H or 1-6C alkyl; R 6>OR 2> or R 2>; m : 0-2, and Q : halo. Independent claims are also included for the following: (1) preparation of (III; W = a protecting group) which comprises reacting a ketone compound of formula (V) with a halogenating agent; (2) preparation of (IV) which comprises reacting (V) with a halogenating agent; (3) preparation of (V) which comprises reacting a ketone compound of formula (VI) with O=CXY in the presence of base; (4) preparation of resorcinol derivatives of formula (VII) which comprises the process (A) as above and reducing (I; W = H) or (II; W = H) or reducing (I; W = protecting group) or (II; W = protecting group) and removing the protecting group; (5) preparation of (VII) which comprises process (A) as above to give (I), reacting (I) with a base to give (II) and hydrogenating (II; W = H), or removing the protecting group from (II; W = protecting group) and hydrogenating the obtained (II; W = H); (6) preparation of (VII) which comprises process (A) as above to give (II) and hydrogenating (II; W = H), or removing the protecting group from (II; W = protecting group) and hydrogenating the obtained (II; W = H); (7) preparation of (II; W = H) as in (5) or (6), and (8) new compounds (V), (III) and (IV). [Image] ACTIVITY : Dermatological. MECHANISM OF ACTION : None given.