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Synlett

Volumn , Issue 8, 2007, Pages 1259-1263

Novel oxidation of substituted pyrrolidines by N-bromosuccinimide - Rapid synthesis of pyrrolo[2,1-a]isoquinolines

(6) Tóth, Judit a Váradi, Linda a Dancsó, András b Blaskó, Gábor b Toke, László a Nyerges, Miklós a

a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS (Hungary)

b EGIS PHARMACEUTICALS LTD (Hungary)

Author keywords

Azomethine ylides; Cycloadditions; Oxidation; Pyrroles

Indexed keywords

5,6 DIHYDROPYRROLO[2,1 A]ISOQUINOLINE DERIVATIVE; N BROMOSUCCINIMIDE; PYRROLIDINE DERIVATIVE; PYRROLO[2,1 A]ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34249811516 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-977461 Document Type: Article

Times cited : (9)

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- General procedure for the preparation of compounds 5a-1: The corresponding cycloadduct (4, 1.0 mmol) was dissolved in CHCl3 (10 mL) and NBS (0.17 g, 1.1 mmol) was added in one portion. The solution immediately turned yellow. After 30 min stirring H2O (10 mL) was added and the organic layer was washed with further portions of H2O (2 x 10 mL) and brine (10 mL, then dried (MgSO4) and evaporated in vacuo. The residue was triturated with cold EtOH and filtered to yield the title product as a yellow powder. All new compounds afforded correct elemental analyses and spectroscopic data. Selected examples: Methyl 8,9-dimethoxy-1- nitro-2-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate (5a, IR (KBr, 2956, 2833, 1700, 1609, 1591, 1561, 1547, 1506, 1452, 1439, 1355, 1284, 1262, 1236, 1217, 1195, 1181, 1136, 1100, 1072, 1016 cm -1; 1H NMR (500 MHz, CDCl3, δ, 7.39 m, 4 H, Ph
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