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 15th 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

Article Metrics

Abstract views : 922 | views : 3496


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.