Patent IL-111511-A (IL)
Title: Tri or tetra substituted allylazetidinone compounds
IPC: C07F7/18
Filed: 1991-02-19
Abstract: A tri or tetra substituted allylazetidinone compound useful as chemical intermediate of the formula R1R2X NY OQ CO2R3 wherein R1 is a hydrogen; a straight-chain or branched lower alkyl group selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, or isopentyl; a straight-chained or branched lower alkoxy group selected from methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, or tert-butoxy; or a R4 B group £wherein R4 is a hydroxyl group; a lower alkoxy group selected from methoxy, ethoxy, n-propoxy, or isopropoxy; fluoride; an acyloxy group selected from acetoxy, propionyloxy, n-butyryloxy, or isobutyryloxy or an aralkyloxycarbonyloxy group selected from benzyloxycarbonyloxy or p-nitrobenzyloxycarbonyloxy; a lower alkylsulfonyloxy group selected from methanesulfonyloxy, ethanesulfonyloxy, or propanesulfonyloxy; an arylsulfonyloxy group selected from benzenesulfonyloxy or p-toluenesulfonyloxy; a lower trialkylsilyloxy group selected from trimethylsilyloxy or tert- butyldimethylsilyloxy; a mercapto group; a lower alkylthio group selected from methylthio, ethylthio, n-propylthio, or isopropylthio; an amino group; or a lower aliphatic acylamino group selected from acetylamino, propionylamino, n-butyrylamino, or isobutyrylamino; and B is an alkylene group that may have trifluoromethyl or phenyl substituents, selected from methylene, ethylene, ethylidene, trimethylene, propylidene, isopropylidene, tetramethylene, butylidene, pentamethylene, pentylidene, 2, 2, 2-trifluoroethylidene, 3, 3, 3-trifluoropropylidene, or benzylidene|; R2 = hydrogen, C1-C6 alkyl, phenyl and C1-C6 alkyl substituted phenyl; R3 is a hydrogen atom; a straight-chain or branched lower alkyl group selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl; a lower haloalkyl group selected from 2-iodoethyl, 2, 2-dibromoethyl, or 2, 2, 2-trichloroethyl; a lower alkoxymethyl group selected from methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, or isobutoxymethyl; a lower aliphatic acyloxymethyl group selected from acetoxymethyl, propionyloxymethyl, n-butyryloxymethyl, isobutyryloxymethyl, or pivaloyloxymethyl; a 1-(lower alkoxy) carbonyloxyethyl group selected from 1-methoxycarbonyloxyethyl, 1-ethoxycarbonyloxyethyl, 1-n- propoxycarbonyloxyethyl, 1-isopropoxycarbonyloxyethyl, 1-n- butoxycarbonyloxyethyl, or 1-isobutoxycarbonyloxyethyl; an aralkyl group selected from benzyl, p-methoxybenzyl, o-nitrobenzyl, or p-nitrobenzyl; a benzhydryl group; a phthalidyl group, a silyl group selected from trimethylsilyl or t-butyldimethylsilyl or 2-trimethylsilylethyl; an allylic group selected from allyl, 2-chloro-2-propenyl, 2-butenyl, 3-methyl-2-butenyl or 2-cinnamyl; Q = a suitable leaving group selected from the group consisting of: F, Cl, Br, I, R21S, R21SO2, NR213, PR213, OR21, OCOR21, OOH, OOR21, -OP(O) (OPh)2, -OP(O)(OCCl3)2, -OSO2Ph, -OSO2(4-nitrophenyl), -OSO2CH3 and CN; R21 = an alkyl group which may be straight or branched chain having 1-10 carbon atoms; a phenyl substituted alkyl group selected from benzyl, benzhydryl CH(C6H6)2, 2-phenylethyl; phenyl, optionally substituted by 1-3 substituents independently selected from fluoro, chloro, bromo, C1-C3 alkyl, SO2R17, CO2R16, or CONR18R19; X = fluorine, chlorine, bromine, iodine; Y = a suitable electron withdrawing group selected from the group consisting of O CO2H, CO2R16, CR17, OS CN, CNR18R19, CNR18R19, SS COR16, CSR16 F, Cl, Br, I; R16 = a straight-chain or branched lower alkyl group selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl; a lower haloalkyl group selected from 2-chloroethyl, 3-chloropropyl, 2-iodoethyl, 2, 2-dibromoethyl or 2,2,2-trichloroethyl; a lower trimethylsilylalkyl group selected from 2-trimethylsilylethyl; a substituted allyl selected from 2-chloro-2-propenyl, 3-methyl-2-propenyl, 3-methyl-2-butenyl, 3-phenyl-2-propenyl; a lower alkyl-t-butyldimethylsiloxy group of 2-4 carbon atoms; a lower alkylhydroxy group of 2-4 carbon atoms; phenyl; an alkylheteroaryl group with 1-3 carbon atoms is the alkyl chain attached to a 5- or 6-membered heteroaryl ring that contains 1-4 O, N or S atoms attached through a ring carbon atoms in the alkyl chain attached to a 5- or 6-membered ring that contains 1-4 O, N or S atoms attached through a ring carbon or ring nitrogen; R17 = (1) a phenyl ring, optionally substituted by 1-3 substituents independently selected from; (1a) halogens (F, Cl, Br, I) or trifluoromethyl; (1b) C1-C4 branched or linear alkyl; (1c) hydroxy or protected hydroxy group, amino or protected amino group, thiol or protected thiol group; (1d) alkenyl and alkynyl groups having 1-4 carbon atoms; (1e) a carboxy or carboxamido group; (1f) a 5- or 6-membered heteroaryl ring that contains 1-4 O, N or S atoms attached through a ring carbon or nitrogen; (1g) a heterocycle group that contains 1-4 O, N or S atoms attached through a ring carbon or nitrogen; (2) a fused phenyl ring, optionally one that is fused to a 5- or 6-membered heteroaryl ring containing 1-3 O, N or S atoms and optionally substituted by 1-3 substituents independently selected from (1a) through (1e) above; (3) a 5- or 6-membered heteroaryl ring that contains 1-4 O, N or S atoms attached through a ring carbon and optionally substituted by 1-3 substituents independently selected from (1a) through (1e) above; or fused to another unsaturated ring selected from a phenyl ring or a 5- to 6-membered saturated or unsaturated heterocyclic ring containing 1-3 O, N or S atoms; R18 and R19 are independently selected from hydrogen; substituted or unsubstituted alkyl having from 1-10 carbon atoms; substituted or unsubstituted cycloalkyl having from 1-10 carbon atoms; aralkyl selected from phenylalkyl and heterocycloalkyl wherein the alkyl has 1-6 carbon atoms and the heteroatom or atoms are selected from O, N and S; and a cyclic group wherein R18 and R19 together form a ring which optionally may be substituted by amino, mono, di- and trialkylamino (each alkyl having 1-6 C atoms), hydroxyl, carboxyl, alkoxy having from 1-6 carbon atoms, halo selected from chloro, bromo, cluoro, nitro, sulfonamido, phenyl, benzyl and alkoxylcarbonyl having 1-3 carbon atoms in the alkoxy moiety.