Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media.
A novel ionic liquid (IL) supported, green synthetic protocol has been developed toward the synthesis of oxo and thio hydantoin analogues tethered with tetrahydro-beta-carboline by the use of focused microwave irradiation. IL-bound tryptophan underwent a Pictet-Spengler reaction with various carbonyl compounds to generate the IL-immobilized tetrahydro-beta-carbolines in aqueous isopropanol media. Subsequent reaction of substituted tetrahydro-beta-carboline derivatives with various isocyanates and isothiocyanate provided a three-dimensional combinatorial library in a traceless fashion.
Maiti
Barnali
B
Laboratory of Combinatorial Drug Discovery, Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300-10, Taiwan.
Chanda
Kaushik
K
Sun
Chung-Ming
CM
D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006827:Hydantoins / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry
D002243:Carbolines; D006827:Hydantoins; D026121:Indole Alkaloids; D014364:Tryptophan