Synthesis of functionalized benzo[1,3]dioxin-4-ones from salicylic acid and acetylenic esters and their direct amidation

Direct synthesis of 4 H -benzo[ d ][1,3]dioxin-4-one derivatives from salicylic acids and acetylenic esters (both mono- and disubstituted) has been described. The reaction is mediated by CuI and NaHCO 3 in acetonitrile. Room temperature amidation of the synthesized 1,3-benzodioxinones with primary a...

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Bibliographic Details
Published in:RSC advances 2021-07, Vol.11 (4), p.2457-24574
Main Authors: Bhaskaran, Rasmi P, Nayak, Kalinga H, Babu, Beneesh P
Format: Article
Language:English
Subjects:
Acetonitrile
Amines
Chemistry
Crystallography
Dioxins
Esters
NMR
Nuclear magnetic resonance
Room temperature
Salicylic acid
Sodium bicarbonate
Synthesis
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Summary:Direct synthesis of 4 H -benzo[ d ][1,3]dioxin-4-one derivatives from salicylic acids and acetylenic esters (both mono- and disubstituted) has been described. The reaction is mediated by CuI and NaHCO 3 in acetonitrile. Room temperature amidation of the synthesized 1,3-benzodioxinones with primary amines readily afforded the corresponding salicylamides in moderate to good yields. An efficient method for the synthesis of the active core 4 H -benzo[ d ][1,3]dioxin-4-one followed by its direct room temperature amidation is reported.
ISSN:2046-2069
2046-2069
DOI:10.1039/d1ra05032j