FIELD: organic chemistry, chemical technology, medicine.
SUBSTANCE: invention relates to the improved method for synthesis of 1,3-substituted indenes that are intermediate compounds used in synthesis of aryl-condensed azapolycyclic compounds used in treatment of neurological and psychological disorders. Method for synthesis of 1,3-substituted indenes of the general formula (I) given in the invention description wherein R1 represents electron-accepting group chosen from the group consisting of cyano-group, alkoxycarbonyl, alkylcarbonyl, aryl, nitro-group, trifluoromethyl and sulfonyl; R2 and R3 are chosen independently from hydrogen atom, (C1-C5)-alkyl, (C1-C5)-alkoxy-group, trifluoromethyl, halogen atom, sulfonylalkyl, alkylamino-group, amide, ester, arylalkyl, heteroalkyl and arylalkoxy-group; or R2 and R3 in common with carbon atoms to which they are bound form monocyclic or bicyclic ring; each R4 represents independently (C1-C6)-alkyl, or two groups of R4 form in common (C2-C3)-alkylene bridge involves the following steps: (a) interaction in the absence of solvent between compound of the formula (II) given in the invention description wherein X is chosen from the group consisting of chlorine, bromine and iodine atoms, and R1, R2 and R3 have above given values with monohydric or dihydric alcohol in the presence of sulfuric acid, and (b) treatment of the reaction product with base and water for neutralization o sulfuric acid residue. As a rule, compound of the formula (II) is synthesized by (a) interaction of compound of the formula (III) given in the invention description wherein R1, R2, R3 and X have above given values with 3-ethocyacrylate in the presence of catalyst and inert water-soluble organic solvent, and (b) complete removal of solvent after termination of indicated reaction. Method provides preparing 1,3-substituted indenes with high yield.
EFFECT: improved method of synthesis.
13 cl, 3 sch, 1 ex
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