| 摘要 |
Three stage synthesis of 3-(4-hydroxy-1H-indol-5-yl)-pyridinium compounds with the exclusion of 3-pyridinecarboxaldehyde compounds. 3-(4-hydroxy-1H-indol-5-ylmethyl)-pyridinium compounds of formula (I) is synthesized by reacting in a solvent the compound of formula (II) with a 3-pyridine metal of formula (III) to obtain an enone derivative of formula (IV). The metal is Mg, Mn, Li, Cu Cd or Zn. The enone is then reacted in a solvent with a quaternizing agent R5X to obtain a cyclohexenone of formula (V). The cyclohexenone is aromatized in a solvent and a base to give the compound (I). R1 = H, 1 - 6C alkyl, 7 - 12C aralkyl, 1 - 6C monohydroxyalkyl, 2 - 6C poly-hydroxyalkyl, (1- 6C alkoxy)1 - 6C alkyl, (1 - 6C alkyl)1 - 6C thioalkyl, (1 - 6C alkoxy)1 - 6C-carbonylalkyl, 1 - 6C cyanoalkyl, 1 - 6C trifluoroalkyl, 1 - 6C halogenoalkyl, 1 - 6C phosphoalkyl or 1 - 6C sulfoalkyl; R2 and R3 = H or halogen, 1 - 6C alkyl, 7 - 12C aralkyl or 1 - 6C alkoxy; R4 = H or halogen, OH, 1 - 6C alkyl, 7-12C aralkyl, 1- 6C monohydroxyalkyl, 2 - 6C polyhydroxyalkyl, NO2, CN, 1 - 6C cyanoalkyl, 1 - 6C alkoxy. (1 - 6C trialkyl)1 - 6C silanealkyl, 1 - 6C alkylcarbonyl, 1 - 6C thioalkyl or 1- 6C alkylthio; R5 = 1 - 6C alkyl, 1 - 6C monohydroxyalkyl, 2 - 6C polyhydroxyalkyl, 7 - 12C aralkyl, aryl, 1 - 6C aminoalkyl, 1 - 6C amino-alkyl with amine protected by 1- 6C alkylcarbonyl, carbamyl or (1 - 6C alkyl)sulfonyl, 1 - 6C carboxyalkyl, 1 - 6C cyanoalkyl, 1- 6C carbamylalkyl, 1 - 6C trifluoroalkyl,(1 - 6C trialkyl)1 - 6C silanealkyl, 1 - 6C sulfonamidoalkyl, (1 - 6C alkyl)1 - 6C sulfinylalkyl, (1 - 6C alkyl)1 - 6C sulfonyl-alkyl, (1 - 6C alkyl)1 - 6C ketoalkyl, (1 - 6C N-alkyl)1 - 6C carbamylalkyl or (1 - 6C N-alkyl 1 - 6C sulfonamidoalkyl; R6 = H or halogen, 1- 6C alkyl, 1 - 6C alkoxy, (1 - 6C alkoxy)1 - 6C alkyl, thiophene, furan, phenyl or 1 - 6C aralkyl; R7 = OH, dialkylamino(optionally cyclic) or 1 - 6C alkoxy ; X = mono- or di-valent anion.
|
