New findings on the Vilsmeier-Haack approach to quinoline derivatives
1993; Elsevier BV; Volume: 49; Issue: 47 Linguagem: Inglês
10.1016/s0040-4020(01)80253-2
ISSN1464-5416
AutoresMiguel Ángel Verdugo Alonso, J. I. UBEDA, Carmen Avendaño, J. Carlos Menéndez, Mercedes Villacampa,
Tópico(s)Synthesis and pharmacology of benzodiazepine derivatives
ResumoThe presence of electron-releasing substituents on the aromatic ring of anilides, although necessary for the Vilsmeier-Haack cyclization to quinolines to proceed efficiently, can cause failure of the expected cyclization, leading to (Z) N,N-dimethylformamidines through an alternative course. A similar behaviour is observed when π-donor groups are introduced on the α position of the anilide, although in this case some cyclization to quinoline derivatives generally occurs.
Referência(s)