Reactivity of Pyrido[4,3,2-kl]acridines: Regioselective Formation of 6-Substituted Derivatives.
Pyrido[4,3,2-kl]acridines, e.g., I, represent a new class of heterocycles, isomers of marine alkaloids. I reacts as an electron rich heterocycle, and in particular via regioselective electrophilic substitution such as H/D exchange and the Vilsmeier-Haack reaction to give the corresponding 6-substituted derivs. Pyrido[4,3,2-kl]acridin-4-one II reacts with amines and thiol, via 1,4-Michael addn. to give the 6-amino or 6-thio analogs in a very efficient way. Mol. calcns. account for the obsd. regioselectivity. [on SciFinder(R)]
Références
- Titre
- Reactivity of Pyrido[4,3,2-kl]acridines: Regioselective Formation of 6-Substituted Derivatives.
- Type de publication
- Article de revue
- Année de publication
- 2004
- Auteurs
- Bouffier, Laurent, Demeunynck Martine, Milet Anne, and Dumy Pascal
- Revue
- J. Org. Chem.
- Volume
- 69
- Pagination
- 8144–8147
- ISSN
- 0022-3263
Soumis le 12 avril 2018