Synthesis of tetrahydro-β-carbolinediketopiperazines in [bdmim][PF 6] ionic liquid accelerated by controlled microwave heating

Tetrahedron Letters

Volumn 45, Issue 44, 2004, Pages 8137-8140

  Yen, Ya Hew ^a   Chu, Yen Ho ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

Ionic liquid; Microwave assisted organic reaction; Tetrahydro carbolinediketopiperazine

Indexed keywords

CARBOLINE DERIVATIVE; ESTER DERIVATIVE; PIPERAZINE DERIVATIVE; TRYPTOPHAN DERIVATIVE;

AMIDATION; ARTICLE; DIPOLE; DRUG SYNTHESIS; MICROWAVE COOKING; MICROWAVE IRRADIATION; PICTET SPENGLER REACTION; VAPOR PRESSURE;

EID: 4744372596     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.056     Document Type: Article

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37. 6]/THF (1:1, v/v; 1 mL) containing 20% (v/v) piperidine to carry out the final cyclization-upon-deprotection reaction at 60°C under microwave irradiation (60 W) condition, again, in an open reaction vessel. The reaction was allowed to proceed until the protected dipeptide ester was completely consumed and cyclized as monitored by TLC (typically 60 s). Upon completion of the total three-step synthesis, the solution mixture containing the desired tetrahydro-β-carbolinediketopiperazine was concentrated in vacuo and purified by silica gel flash column chromatography (ethyl acetate/hexane = 1:3). The products were afforded as off-white solid
38. 4 it appeared that in this work our three-step synthesis of tetrahydro-β- carbolinediketopiperazines from tryptophan methyl ester carried out at ambient temperature and under low-power microwave irradiation gave no apparent similar preference for a particular product isomer