Rhodium‐Catalyzed Functionalization and Annulation of N‐Aryl Phthalazinediones with Allyl Alcohols
A direct ortho-Csp<sup>2</sup>-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)<sub>2</sub>⋅2H<sub>2</sub>O 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.
Authors
- Sushma Naharwal
- Siva Sankar Panda (ORCID: https://orcid.org/0000-0003-3668-104X)
- Rajeev Sakhuja (ORCID: https://orcid.org/0000-0002-9284-9137)
- Kiran Bajaj (ORCID: https://orcid.org/0000-0003-4483-4747)
- Narendra Dinkar Kharat
Institutions
- Amity University (IN)
- Augusta University (US)
- Augusta University Health (US)
- Birla Institute of Technology and Science, Pilani (IN)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2024-08-23
- DOI
- https://doi.org/10.1002/asia.202400711
- Citations
- 3
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Birla Institute of Technology and Science, Pilani