2022
DOI: 10.1002/slct.202203072
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Ultrasound‐Assisted Green Synthesis of 3,5‐Disubstituted Isoxazole Secondary Sulfonamides via One‐Pot Five‐Component Reaction using CaCl2/K2CO3 as Pre‐Catalyst in Water

Abstract: Tandem one-pot five-component reaction involving saccharin, propargyl bromide, aldehyde, hydroxylamine hydrochloride, and non-conjugated primary amine has been explored for a rapid and an efficient synthesis of isoxazole-secondary sulfonamides. This novel multicomponent reaction involves one pot Npropargylation of saccharin, oximation, and 1,3-dipolar cycloaddition, followed by an intermolecular ring-opening reaction by N-nucleophilic amine. This transformation is catalyzed by CaCl 2 /K 2 CO 3 and activated un… Show more

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Cited by 5 publications
(3 citation statements)
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“…The nitrile oxide was then trapped by the N ‐allyl‐saccharin 3 (1equiv.) prepared using our previously reported method 54 as a dipolarophile via the 1,3‐dipolar cycloaddition to form the 3,5‐disubstituted isoxazoline‐saccharin as expected intermediate 4a–f under ultrasound cavitation. Then, the obtained products 4a–f were reacted with non‐conjugated primary amines 5a–f (2 equiv.)…”
Section: Resultsmentioning
confidence: 99%
“…The nitrile oxide was then trapped by the N ‐allyl‐saccharin 3 (1equiv.) prepared using our previously reported method 54 as a dipolarophile via the 1,3‐dipolar cycloaddition to form the 3,5‐disubstituted isoxazoline‐saccharin as expected intermediate 4a–f under ultrasound cavitation. Then, the obtained products 4a–f were reacted with non‐conjugated primary amines 5a–f (2 equiv.)…”
Section: Resultsmentioning
confidence: 99%
“…Today in the modern methodology used in the preparation of the amide using green chemistry, the synthetic procedure includes the reaction carried out in conditions water [25], microwave [26], ultrasound [27], electro synthesis [28].…”
Section: Beckmann Rearrangement Of Oximesmentioning
confidence: 99%
“…Therefore, finding a green and efficient source for the synthesis of secondary sulfonamide derivatives should be a priority. Our research group has recently developed the synthesis of a new series of heterocyclic units bearing secondary sulfonamides using an eco-friendly protocol under ultrasound cavitation [12,13].…”
Section: Introductionmentioning
confidence: 99%