Ruthenium Catalyzed C-H Acylmethylation of N-Arylphthalazine-1,4-diones with α-Carbonyl Sulfoxonium Ylides: Highway to Diversely Functionalized Phthalazino-fused Cinnolines
| Autor: | Pidiyara Karishma, Rajeev Sakhuja, Sanjay K. Mandal, Devesh S. Agarwal, Biswajit Laha |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Aryl Organic Chemistry chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis Ruthenium Solvent chemistry.chemical_compound chemistry Transition metal Reagent Functional group Methylene |
| Zdroj: | Chemistry, an Asian journal. 14(23) |
| ISSN: | 1861-471X |
| Popis: | A direct ortho-Csp2 -H acylmethylation of 2-aryl-2,3-dihydrophthalazine-1,4-diones with α-carbonyl sulfoxonium ylides is achieved through a RuII -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. |
| Databáze: | OpenAIRE |
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