Palladium-catalysed regioselectiveN-arylation of anthranilamides: a tandem route for dibenzodiazepinone synthesis
| Autor: | Mandeep Kaur Hunjan, Joydev K. Laha, Neelam Manral |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Tandem
chemistry.chemical_element Regioselectivity 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Combinatorial chemistry Catalysis Domino 0104 chemical sciences chemistry.chemical_compound chemistry Amide Materials Chemistry Amine gas treating 0210 nano-technology Palladium |
| Zdroj: | New Journal of Chemistry. 43:7339-7343 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c9nj00539k |
| Popis: | A palladium-catalyzed domino approach to the synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepinones from 2-aminobenzamides and 1,2-dihaloarenes has been developed. Our strategy integrating double N-arylations (inter- and intra-molecular) of 2-aminobenzamides with 1,2-dihaloarenes under palladium-catalyzed conditions is clearly distinct from the current literature available for the synthesis of dibenzodiazepinones. Unlike a previous report described for regioselective N-arylation of 2-aminobenzamide at the amine group, our mechanistic studies support the regioselective N-arylation of 2-aminobenzamide occurring first primarily at the amide group. The translational application of our protocol may be demonstrated in the synthesis of a marketed drug, clozapine. |
| Databáze: | OpenAIRE |
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