FIELD: organic synthesis.
SUBSTANCE: invention provides methods for preparing lamellarine compounds of general formula II: (II) via intramolecular cyclization of compounds having general formula I: (I), in which formulas moiety RA1RA2C-CRA3RA4 forms optionally monosubstituted aryl group or optionally monosubstituted aromatic 3-6-membered heteromonocyclic group with one nitrogen atom; Y represents hydrogen atom, optionally monosubstituted C1-C20-alkyl, optionally monosubstituted C2-C20-alkenyl, optionally monosubstituted C2-C20-alkynyl, hydroxy, optionally monosubstituted amino, optionally monosubstituted C1-C20-alkoxy, optionally monosubstituted C1-C20-alkenoxy, optionally monosubstituted C1-C20-alkynoxy, optionally monosubstituted aryl, optionally monosubstituted saturated or unsaturated 3-6-membered heteromonocyclic group with one nitrogen atom, carboxy, carboxyester, carboxamide, C1-C20-acyl, C1-C20-acyloxy, mercapto, optionally monosubstituted C1-C20-alkylthio, halogen, nitro, sulfate, phosphate, or cyano; W and X, together with nitrogen and carbon atoms to which they are linked, form group selected from quinoline, isoquinoline, dehydroquinoline, and pyridyl groups all optionally monosubstituted, dihydro- or tetrahydro-derivatives of indicated groups, and optionally monosubstituted phenantridine; wherein optional substituent is selected from C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, aryl, halogen, halo-C1-C20-alkyl, halo-C2-C20-alkenyl, halo-C2-C20-alkynyl, haloaryl, hydroxy, C1-C20-alkoxy, C2-C20-alkenyloxy, aryloxy, benzyloxy, halo-C1-C20-alkoxy, halo-C1-C20-alkenyloxy, haloaryloxy, nitro, nitro-C1-C20-alkyl, nitro-C2-C20-alkenyl, nitro-C2-C20-alkynyl, nitroaryl, nitro-substituted 3-6-membered heteromonocyclic group with one nitrogen atom, amino, C1-C20-alkylamino, di-C1-C20-alkylamino, C2-C20-alkenylamino, C2-C20-alkynylamino, arylamino, diarylamino, benzylamino, dibenzylamino, C1-C20-acyl, C2-C20-alkenylacyl, C2-C20-alkynylacyl, arylamino, diarylamino, benzylamino, dibenzylamino, C1-C20-acyl, C2-C20-alkenylacyl, C2-C20-alkynylacyl, arylacyl, C1-C20-acylamino, di-C1-C20-acylamino, C1-C20-acyloxy, C1-C20-alkylsulfonyloxy, arylsulfenyloxy, 3-6-membered heteromonocyclic group with one nitrogen atom, oxy-, amino-, and halogen-derivatives of the latter, C1-C20-alkylsulfenyl, arylsulfenyl, carbo-C1-C20-alkyloxy, carbo-C6-C24-aryloxy, mercapto, C1-C20-alkylthio, benzylthio, C1-C20-acylthio, cyano, sulfate, and phosphate; V represents halogen, hydrogen, or oxygen atom; and intermediates having general formulas Ia and Ib:
EFFECT: expanded synthetic possibilities in lamellarine series.
28 cl, 1 dwg, 2 tbl
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Authors
Dates
2005-04-20—Published
1999-06-25—Filed