METHOD OF PREPARING 1,3-DIMETHYL-4,8-DIALCOXY-6-R-PYRROLO(THIENO)-[C]- TROPILIUM SALTS

FIELD: organic synthesis. SUBSTANCE: compounds of general formula I: (I) wherein Z is S, N-H, N-R (R is C1-C10-alkyl, C1-C10-alkoxy, and carbethoxy radicals); R1 is hydrogen atom, styryl, phenyl, mono- or dihydroxyphenyl, mono- or dihydroxy-C1-C10-alkoxy, methylenedioxy, and di-C1-C6-alkylamino grou...

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Hauptverfasser: BOROSHKO S.L, OLEKHNOVICH E.P, OLEKHNOVICH L.P, ZHDANOV JU.A
Format: Patent
Sprache:eng
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Zusammenfassung:FIELD: organic synthesis. SUBSTANCE: compounds of general formula I: (I) wherein Z is S, N-H, N-R (R is C1-C10-alkyl, C1-C10-alkoxy, and carbethoxy radicals); R1 is hydrogen atom, styryl, phenyl, mono- or dihydroxyphenyl, mono- or dihydroxy-C1-C10-alkoxy, methylenedioxy, and di-C1-C6-alkylamino groups; R2 is C1-C10=alkyl; and X is ClO4, HSO4, or Br; are prepared by heating 3,4-diacetylhexanedione (formula II: (II)) with hydrogen sulfide in acetic acid or by melting it with alkylamines, arylamines, their acetate salts, or ammonium acetate to form 2,5-dimethyl-3,4-diacetylpyrrols(thiophenes), which, in the same reactor or after intermediate isolation from reaction mixture, are brought into interaction with trialkyl-ortho-formiates and inorganic acid (to form compounds I with R1 = H) or with aromatic aldehydes R1- CHO in presence of perchloric acid followed by treatment with trialkyl- ortho-formiate (to form compounds I with R1 = styryl, or optionally substituted phenyl). Compounds I are potential biologically active compounds, which manifest high reactivity in reactions with nucleophils and can be used for production of various known and new biologically active compounds of pyrrolo(thyeno)-[C]-tropilium and azaazulene types. EFFECT: extended choice of biologically active compounds. 7 cl, 2 tbl, 21 ex