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A Novel Synthesis of Isoflavones via Copper(I)-Catalyzed Intramolecular Cyclization Reaction

✍ Scribed by Qiu-Lian Li; Qi-Lun Liu; Zhi-Yuan Ge; Yong-Ming Zhu

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
155 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Isoflavone derivatives were synthesized via intramolecular cyclization of 3-(2-bromophenyl)-3oxopropanal derivatives, using CuI as the catalyst, 2-picolinic acid (ΒΌ pyridine-2-carboxylic acid) as the ligand, K 2 CO 3 as the base, and DMF as the solvent, in up to 96% yield. The synthesis is functional grouptolerant.

a ) All the reactions were run with 1 (0.5 mmol), in the presence of 10 mol-% of catalyst and 20 mol-% of ligand, and 200 mol-% of base at 135 -1408 under N 2 for 20 h. b ) Yields after chromatography. c ) At 70 -808. d ) Under reflux.

πŸ“œ SIMILAR VOLUMES

A Novel and Regiospecific Synthesis of 1
A Novel and Regiospecific Synthesis of 1-Aryl-1H-benzotriazoles via Copper(I)-Catalyzed Intramolecular Cyclization Reaction
✍ Qi-Lun Liu; Di-Di Wen; Chen-Chen Hang; Qiu-Lian Li; Yong-Ming Zhu πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons 🌐 German βš– 164 KB

## Abstract 1‐Aryl‐1__H__‐benzotriazole derivatives were synthesized __via__ intramolecular cyclization of easily obtained triazenes, using CuI as the catalyst, DMSO as the solvent, __t‐__BuONa as the base, and 1,10‐phenanthroline as the ligand, in up to 97% yield. The synthesis is regiospecific an