Synthesis of 2‑Aryl-1,2-dihydrophthalazines via Reaction of 2‑(Bromomethyl)benzaldehydes with Arylhydrazines

Synthesis of 2‑Aryl-1,2-dihydrophthalazines via Reaction of 2‑(Bromomethyl)benzaldehydes with Arylhydrazines

The reaction of 2-(bromomethyl)benz­aldehydes with arylhydrazines employing K2CO3 as a base and FeCl3 as a catalyst in CH3CN at 100 °C delivers 2-aryl-1,2-dihydrophthalazines with yields ranging from 60 to 91%. The transformation is considered to proceed as an intermolecular condensation/intramolecu...

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Veröffentlicht in:Journal of organic chemistry 2013-02, Vol.78 (3), p.1045-1053
Hauptverfasser: Aljaar, Nayyef, Conrad, Jürgen, Beifuss, Uwe
Format: Artikel
Sprache:eng
Schlagworte:
Benzaldehydes - chemical synthesis
Benzaldehydes - chemistry
Catalysis
Molecular Structure
Phthalazines - chemical synthesis
Phthalazines - chemistry
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Zusammenfassung:The reaction of 2-(bromomethyl)benz­aldehydes with arylhydrazines employing K2CO3 as a base and FeCl3 as a catalyst in CH3CN at 100 °C delivers 2-aryl-1,2-dihydrophthalazines with yields ranging from 60 to 91%. The transformation is considered to proceed as an intermolecular condensation/intramolecular nucleophilic substitution.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302491x