Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 11, Pages 5769-5781Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00570
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- Council of Scientific and Industrial Research (CSIR), New Delhi, India
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This work reports tert-butyl nitrite (TBN) as a. multitask reagent for (1) the controlled synthesis of N-nitrosoamide from N-alkyl amides, (2) hydrolysis of Nmethoxyamides to carboxylic acids, (3) metal- and oxidant-free benzocoumarin synthesis from ortho-aryl-N-methoxyamides via N-H, C=N, and C-H bond activation, and (4) isocoumarin synthesis using Ru(II)/PEG as a recyclable catalytic system via ortho-C-H activation and TBN as an oxygen source. The sequential functional, group interconvetsion of amide to acid has also been examined using IR spectroscopic analysis. Additionally, this methodology is highly advantageous due to short reaction time, gram scale synthesis, and broad substrate scope.
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