SYNTHESIS OF THE ISOQUINO-[2,1-c][1,3]-BENZODIAZEPINE DERIVATIVE FROM PAPAVERINE

I Made Sudarma (Laboratorium Kimia, Universitas Mataram, Jl. Majapahit 62 Mataram 83125)
John Bremner (University of Wollongong, Northfields Avenue, N.S.W Australia 2522)

Indonesian Journal of Chemistry
Vol 7, No 3 (2007)

The objective of this research was to synthesize isoquino[2,1-c][1,3]benzodiazepine from papaverine alkaloid. Functional Group Interconversion (FGI) and Carbon -Nitrogen bond connection approach was investigated. Papaverine (1) was nitrated by HNO3 to compound (2) and followed by reduction with Sn and HCl to afford aminonorlaudanosine (3). Formation of cyclic benzodiazepine (4) was achieved by reaction of (3) with CS2. Products of reactions were confirmed by Nuclear Magnetic Resonances (n.m.r), Mass Spectrum, and Fourier Transform Infra Red (FTIR).