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

I Made Sudarma; John Bremner

doi:10.22146/ijc.21677

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

https://doi.org/10.22146/ijc.21677

I Made Sudarma^(1*), John Bremner⁽²⁾

(1) Laboratorium Kimia, Universitas Mataram, Jl. Majapahit 62 Mataram 83125
(2) University of Wollongong, Northfields Avenue, N.S.W Australia 2522
(*) Corresponding Author

Abstract

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).

Keywords

isoquino[2,1-c][1,3]benzodiazepine; papaverine

Full Text:

Full Text PDF

References

[1] Shamma, M., 1982, The Isoquinoline Alkaloid, Chemistry and Pharmacology, Academic Press, New York, vol. 25, 194 – 228.

[2] Shamma, M., and Moniot, M., 1988, Isoquinoline Alkaloids Research 1972–1977. Plenum Press, New York. P 123 -154

[3] Sudarma, I.M., 2006, Jurnal Penelitian Universitas Mataram, 2 (9}, 50 – 54.

[4] Sudarma, I.M., 2007, Indo. J. Chem., 7 (1), 67 - 71.

[5] Martinez, M. and Angeles, A., 1995, In Abstract 15^th International Congress of Heterocyclic Chemistry, Taipei International Convention Center, August 6 –11, PO1 - 05

[6] Spangler R.J., Boop, D.C. and Kim, J.H., 1974, J. Org Chem., 39, 1368.

DOI: https://doi.org/10.22146/ijc.21677