Access to N-Fused Quinazolinones by Radical-Promoted Cascade Annulations of Alkenyl <i>N</i>-Cyanamides with Aromatic Aldehydes
Chada Raji Reddy, Anootha Neeliveettil, Uprety Ajaykumar, Nagender Punna, Luc Neuville, Géraldine Masson
Abstract
A cascade radical cyclization of alkenyl N -cyanamides with aromatic aldehydes has been achieved for an expeditious synthesis of keto-methylated dihydropyrrolo-quinazolinones. Benzoyl radicals, generated from aryl aldehydes in the presence of di- tert -butyl peroxide (DTBP), promoted the domino annulations leading to distinctive functionalized quinazolinones in good yields. In addition, the robustness of the present protocol is validated by employing heterocyclic and natural product-based aldehydes.
Topics & Concepts
CascadeChemistryOrganic chemistryMedicinal chemistryCombinatorial chemistryChromatographyQuinazolinone synthesis and applicationsPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Biological Evaluation