Work

Rhodium‐Catalyzed Functionalization and Annulation of N‐Aryl Phthalazinediones with Allyl Alcohols

Year: 2024

Type: article

Abstract: A direct ortho‐Csp2‐H acylalkylation of 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with unsubstituted and substituted allyl alcohols is achieved in high yields through Rh(III)‐catalyzed C−H bond activation process. The additional employment of Cu(OAc)2⋅2H2O as an oxidant detour the reaction towards [4+1] annulation, producing 13‐(2‐oxopropyl)‐13H‐indazolo[1,2‐b]phthalazine‐6,11‐diones in moderate yields. Interestingly, Lawesson's reagent‐mediated conditions accomplished intramolecular cyclization in ortho‐(formylalkylated)‐2,3‐dihydrophthalazine‐1,4‐diones to produce diazepino[1,2‐b]phthalazine‐diones in moderate yields. Furthermore, allyl alcohol showcased distinct reactivity in presence of different additives to produce ortho‐allylated, oxidative and non‐oxidative [4+2] annulated products.

Source: Chemistry - An Asian Journal

DOI: 10.1002/asia.202400711

Authors: Sushma Naharwal, Narendra Dinkar Kharat, Kiran Bajaj, Siva S Panda, Rajeev Sakhuja

Institutions: Birla Institute of Technology and Science, Pilani, Amity University, Augusta University

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Birla Institute of Technology and Science, Pilani

OpenAlex ID: W4401824942

FWCI: 0.565

Cites: 51

Cited by: 4

Related to: 10