Ruthenium Catalyzed C−H Amidation and Carbocyclization using Isocyanates: An Access to Amidated 2‐phenylphthalazine‐1, 4‐diones and Indazolo[1, 2‐b]phthalazine‐triones. Issue 3 (23rd November 2020)

• Record Type: Journal Article
• Authors: Karishma, Pidiyara; Gogia, Alisha; Mandal, Sanjay K.; Sakhuja, Rajeev
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 3(2021)
• Page Start: 762
• Page End: 775
• Publication Date: 2020-11-23
• Subjects: C−H Activation -- Transition-metals -- Carbonylation -- Catalysis -- C−H Functionalization; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202001146
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A direct carbocyclization of 2‐aryl‐2, 3‐dihydrophthalazine‐1, 4‐diones is achieved using isocyanates as carbonyl source via Ru(II)‐catalyzed sequential ortho ‐amidation followed by intramolecular nucleophilic substitution, delivering substituted indazolo[1, 2‐ b ]phthalazine‐triones in good‐to‐excellent yields. For ortho ‐substituted 2‐aryl‐2, 3‐dihydrophthalazine‐1, 4‐diones, the corresponding amidated products were also isolated in excellent yields by modifying the reaction parameters. Application of isocyanates as carbonyl source, high functional group tolerance on the two coupling partners and diverse chemical transformation of the synthesized fused and functionalized phthalazinones are the key highlights of the work. Abstract :