Direction of bromination and nitration of deoxypeganine and its hydrochloride using HPTLC. Synthesis of 6-bromo(nitro)-, 6,8-dinitrodeoxyvasicinones, 6-nitro(bromo)-, 6,8-dinitrodeoxypeganines,and 6H(bromo)peganols

The reaction of deoxypeganine (DOP) (1) and its hydrochloride (DOP·HCl) (2) with N-bromosuccinimide and a nitrating mixture was studied. It was found that bromination of DOP occurred at C-4 and the aromatic ring. Nitration of DOP·HCl produced either 6-nitro- or 6,8-dinitro-deoxypeganines and 6-nitrodeoxyvasicinone or their mixture in various ratios depending on the substrate:nitrating mixture ratio. 6Hand 6-Br-deoxypeganines were transformed into the 4-hydroxy derivatives, 6H(Br) peganols or deoxyvasicinones. A method for qualitative and quantitative analysis of the pure compounds and the mixture of reaction products using HPTLC was developed. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 505–509, September-October, 2008. Original article submitted March 26, 2008.