2016
DOI: 10.1007/s10593-016-1958-8
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Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides

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Cited by 11 publications
(7 citation statements)
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“…Based on these reactions, mild and efficient approaches to substituted pyridines, furans, pyrroles, and some important azoles using heteroatom-containing unsaturated compounds as starting materials have been developed. [1][2][3][4][5][6] In recent decades, MCCA have drawn great attention and have been exploited to synthesize new functional polymers because of their high atom efficiency, shorter reaction time and higher overall yields than multiple-step syntheses. [7][8][9] Furthermore, MCCA can introduce some special functional groups which largely enrich the functions and diversities of compounds.…”
Section: Introductionmentioning
confidence: 99%
“…Based on these reactions, mild and efficient approaches to substituted pyridines, furans, pyrroles, and some important azoles using heteroatom-containing unsaturated compounds as starting materials have been developed. [1][2][3][4][5][6] In recent decades, MCCA have drawn great attention and have been exploited to synthesize new functional polymers because of their high atom efficiency, shorter reaction time and higher overall yields than multiple-step syntheses. [7][8][9] Furthermore, MCCA can introduce some special functional groups which largely enrich the functions and diversities of compounds.…”
Section: Introductionmentioning
confidence: 99%
“…The starting chloroximes 5 – 9 [both ( R )‐ and ( S )‐isomers were used in the case of chiral compounds] and enamines 10 – 18 were prepared according to the known procedures. Existing literature protocols for the [3+2] cycloaddition of halogenoximes and “push‐pull“ enamines varied in the reaction conditions, including AcOH in dioxane–H 2 O, neat Et 3 N, NaHCO 3 in EtOAc,, , and no promoter in dioxane , . In this work, we have used the conditions described in our previous works for similar transformations of the chloroximes 5 – 9 , , .…”
Section: Resultsmentioning
confidence: 99%
“…The known methods for the synthesis of 4‐(het)arylisoxazoles include palladium‐catalyzed C–C couplings,, , various heterocyclizations and recyclizations, diazotative deamination of the corresponding 5‐aminoisoxazoles, and formal [3+2] cycloaddition of alkynes, electron‐deficient enamines or their synthetic equivalents with halogenoximes , . The latter approach can be considered as the most convenient since generally, the target products are obtained in good yields with high regioselectivity.…”
Section: Introductionmentioning
confidence: 99%
“…The synthesis of N , N -dimethylenaminones 1a–o , q , r was described earlier. , Sulfonyl azides 2a–c , e were prepared from the corresponding sulfonyl chlorides . Compound 2d was obtained according to ref .…”
Section: Methodsmentioning
confidence: 99%
“…Optimal conditions were determined, and methods were developed for the selective and effective synthesis of azoloyl NH-1,2,3-triazoles 4 and diazoketones 5. As an enaminone substrate, we initially selected the earlier synthesized 44,45 N,N-dimethylenaminones 1a−o, as well as enaminone 1p [which we first obtained in two stages via 4acetyl-1,2,3-triazole 9 from Zidovudine (8)] (Scheme 3), where the substituent at position 1 of 1,2,3-triazole widely varied in electronic properties. In addition to 1,2,3-triazole derivatives 1a−p, one representative of the 1,2,3-thiadiazole 1q and isoxazole 1r 45 series were chosen for the study.…”
Section: ■ Introductionmentioning
confidence: 99%