Synthesis and isolation of nitro-beta-carbolines obtained by nitration of commercial beta-carboline alkaloids

Citation
Ma. Ponce et R. Erra-balsells, Synthesis and isolation of nitro-beta-carbolines obtained by nitration of commercial beta-carboline alkaloids, J HETERO CH, 38(5), 2001, pp. 1071-1082
Citations number
64
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
5
Year of publication
2001
Pages
1071 - 1082
Database
ISI
SICI code
0022-152X(200109/10)38:5<1071:SAIONO>2.0.ZU;2-Y
Abstract
Nitration of commercial full aromatic beta -carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitr ation reagents which involve acidic conditions (HNO3/H+) and neutral condit ions (Cu(NO3)(2); ceric ammonium nitrate) are discussed. A complete H-1 and C-13-nmr characterization including ms and also uv absorption spectra in n eutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-beta -carbolines constitute a new family of bet a -carboline-like chromophores with potential use as matrix in uv-maldi-tof -ms.