Ruthenium Catalyzed C−H Acylmethylation of N‐Arylphthalazine‐1, 4‐diones with α‐Carbonyl Sulfoxonium Ylides: Highway to Diversely Functionalized Phthalazino‐fused Cinnolines. Issue 23 (6th November 2019)

• Record Type: Journal Article
• Authors: Karishma, Pidiyara; Agarwal, Devesh S.; Laha, Biswajit; Mandal, Sanjay K.; Sakhuja, Rajeev
• Is Part Of: Chemistry, an Asian journal. Volume 14:Issue 23(2019)
• Page Start: 4274
• Page End: 4288
• Publication Date: 2019-11-06
• Subjects: catalysis -- C−H Activation -- cyclization -- transition metals -- ylides; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201901250
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: A direct ortho ‐Csp 2 ‐H acylmethylation of 2‐aryl‐2, 3‐dihydrophthalazine‐1, 4‐diones with α‐carbonyl sulfoxonium ylides is achieved through a Ru II ‐catalyzed C−H bond activation process. The protocol featured high functional group tolerance on the two substrates, including aryl‐, heteroaryl‐, and alkyl‐substituted α‐carbonyl sulfoxonium ylides. Thereafter, 2‐( ortho ‐acylmethylaryl)‐2, 3‐dihydrophthalazine‐1, 4‐diones were used as potential starting materials for the expeditious synthesis of 6‐arylphthalazino[2, 3‐ a ]cinnoline‐8, 13‐diones and 5‐acyl‐5, 6‐dihydrophthalazino[2, 3‐ a ]cinnoline‐8, 13‐diones under Lawesson's reagent and BF3 ⋅OEt2 mediated conditions, respectively. Of these, the BF3 ⋅OEt2 ‐mediated cyclization proceeded in DMSO as a solvent and a methylene source via dual C−C and C−N bond formations. Abstract : A Ru‐catalyzed ortho ‐acylmethylation and subsequent cyclization is reported.