Synthesis of bicyclic systems containing fused sulfolane and isoxazolidine rings
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Sulfolane
Isoxazole
Hydroxylamine
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Reaction between aryl 1,3-diketoesters 2a-e and hydroxylamine hydrochloride has been investigated under different experimental conditions. Whereas acid conditions gave principally 3,5-isoxazole esters (3a-e), reactions under neutral and basic conditions led to different 4,5 and 2,3-dihydro-hydroxy-isoxazoles 4a-e and 5a-e. Keywords: Isoxazoles, dihydro-hydroxy-isoxazoles, aryl 1,3-diketoesters, hydroxylamine
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Abstract Während die N‐Oxoalkyl‐triazole (I) mit Hydrazinhydrat zu den Ketazinen (II) reagieren, werden aus den N‐0x0‐ " alkyltriazolen (III) mit S‐ständigem Brom‐ oder Nitro‐Substituenten unter Ringschluß die Triazolo‐dihydro‐triazine und ‐triazepine (V) erhalten.
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A novel one-step and high-yield isoxazole formation of 2-aroylcyclohex-2-enones is described. Treatment of such an enone with hydroxylamine under acidic conditions (NH2OH·HCl in EtOH) gave the corresponding 3-aryl-6, 7-dihydro [2, 1] benzisoxazole. Changes in the reaction conditions caused marked changes in the course of the reaction. A possible mechanism for these reactions is put forward.
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Abstract A reaction of 2‐(2‐nitrobenzoylmethyl)‐1,3‐dioxolane ( 3 ) with hydroxylamine, followed by acid catalyzed cyclization, produced 5‐(2‐nitrophenyl)isoxazole ( 5 ) as the only isolable product, whereas 2‐(benzoylmethyl)‐1,3‐dioxolane ( 9 ) under identical conditions produced a 2.5:1 mixture of 3‐phenyl and 5‐phenylisoxazoles 10 and 11 . These findings contradict the literature report that β‐keto ethyleneacetals on treatment with hydroxylamine produce exclusively 3‐substituted isoxazoles. As an additional proof, 3‐(2‐nitrophenyl)isoxazole ( 8 ) was prepared by an unambiguous method via the nitrile oxide route for comparison. The intermediate obtained on treatment of 2‐(2‐nitrobenzoylmethyl)‐1,3‐dioxolane ( 3 ) with hydroxylamine was found to be an isomeric mixture of 5‐hydroxy‐5‐(2‐nitrophenyl)‐2‐isoxazoline ( 4 ) and the syn and anti mono‐oximes 19 (at least in solution), either of which could give 5‐(2‐nitrophenyl)isoxazole ( 5 ) on acid treatment. A mechanistic rationale is provided to explain the anomalous results.
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Investigated additives,heating temperature and time on the thermal stability of sulfolane,and used the content of released SO2 as the final evaluation of the sulfolane thermal stability.The results showed that under the experimental conditions of the absorption in water vapor,nitrogen protection,230 ℃ heating 2 h,the additives E has the best effect.When add the amount of 0.04% of the sulfolane,the sulfolane decomposition of BaSO4 and emission SO2 least,the emission is 10.99 mg.
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Hydroxylamine Hydrochloride
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Abstract Thienyl trichloroallyl ketone (I), a synthetic equivalent of β‐chlorovinyl ketones, reacts with hydroxylamine to an intermediate dichloromethyl‐substituted isoxazole which upon reaction with a second hydroxylamine molecule affords the hydoxyiminomethyl‐substituted isoxazole (II).
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