2016
DOI: 10.1039/c6ra02365g
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A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics

Abstract: An easy access to a large panel of aminoisoxazoles starting from commonly available amino acids.

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Cited by 31 publications
(28 citation statements)
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“…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%
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“…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%
“…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 , , . Thus, treatment of 5 – 9 with NaHCO 3 in EtOAc at room temp., followed by addition of 10 – 18 and subsequent stirring at room temp.…”
Section: Resultsmentioning
confidence: 99%
“…Reported protocols for the reaction of halogenoximes and active methylene nitriles vary significantly in conditions, particularly with respect to the choice of base, which has included Et 3 N,, NaOH, MeONa, EtONa,, , lithium diisopropylamide (LDA), and t BuLi, For our purposes, we initially chose active methylene nitriles 5a – 5h (available from commercial sources) and chloroximes 6a – 6e [preparation previously reported by our group; ( S ) and ( R ) isomers were used to prepare chiral compounds 6b and 6c ] as our model substrates (Figure ). We focused on the use of less nucleophilic bases to extend the possible scope of the reaction.…”
Section: Resultsmentioning
confidence: 99%
“…Her first degree was in agricultural biotechnology at the Agricultural University of Athens. Antidepressants and anxiolytics are classified as:a )selectives erotonin reuptake inhibitors (SSRIs), targeting serotonin; [26][27][28][29][30] b) serotonin and norepinephrine reuptake inhibitors (SNRIs, often called atypical), targeting neurotransmitters other than serotonin or in addition to that;c )tricyclics (TCAs), heterocyclesi nhibiting the reuptake of serotonin and norepinephrine and only partially dopamine; [31] d) tetracyclics (TeCAs), usually used for both depression and anxiety; [32] e) 5-HT 2 or 5-HT 3 serotonin receptor antagonists, usually prescribed for depression; [31] and f) monoamine oxidase inhibitors (MAOIs), interfering with certain foods and drinks,t hus presenting al ife-threatening risk. She has participated in many national and international conferences, is fluent in English and French, and has working knowledge of Spanish.…”
Section: Psychoactive Drugs (Psychotropics)mentioning
confidence: 99%