SYNTHESIS AND MECHANISM STUDY OF NEW BIVALENT β-CARBOLINE DERIVATIVES (Kajian Sintesis dan Mekanisma Derivatif Bivalen β-karbolin Baharu)

Abstract

This study reports simple and straightforward methods for synthesizing new bivalent β-carboline compounds using L-tryptophan as a starting material with 1,4-dibromobutane as a dimerization linker. The synthetic route began with coupling L-tryptophan with formaldehyde via Pictet-Spengler condensation to afford tetrahydro-β-carboline, T1 as the key intermediate. The reaction proceeded with decarboxylation of T1 using potassium dichromate with acetic acid to afford β-carboline, T2. Subsequent alkylation of T2 using 1,4-dibromobutane as the linker yielded intermediate T3, followed by dimerization to furnish the new bivalent β-carboline, T4. 1H and 13C NMR confirmed all the synthesized compounds. In addition, this study includes the proposed mechanism for the synthesis of a new bivalent β-carboline compound.