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To the suspension of 1,2,3,4-tetrahydro-beta-carboline (7, 1.2 mmol) in CH2Cl2 (3 ml) at 0C was added slowly an aqueous solution of 4N NaOH (1.2 mol). After 5 min stirring at 0C, appropriate heterocyclic acid chloride (1.2 mmol) was added dropwise. Mixture was stirred for 15 min at 0C and further stirred at rt for 3 h. Completion of the reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with CH2Cl2 and was washed with water. Organic layer was separated and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure and crude product was purified by silica gel (100-200)column chromatography using EtOAc: Hexane as mobile phase to get desired 2-heterocyclecarbonyl substituted 1,2,3,4-tetrahydro-beta-carbolines 9a-m in 63-82% yield.
Add 5-chlorobenzoisoxazole (1mmol), 2,3,4,9-tetrahydro-1hydro-pyridine[3,4-b]indole (1mmol) and 4mL toluene to a 15mL pressure-resistant tube Medium, stirred at 130 C, reacted for 1 hour,Silica gel column chromatography gave 3b in a yield of 73%.
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