2010
DOI: 10.1002/adsc.201000668
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Synthesis of 2,4‐ and 2,5‐Disubstituted Oxazoles via Metal‐ Catalyzed Cross‐Coupling Reactions

Abstract: The rapid synthesis of 2,4-and 2,5-disubstituted oxazoles via metal-catalyzed cross-coupling reactions is reported. The 4-or 5-position of the corresponding 4-or 5-halogenated 2-butylthiooxazoles was successfully functionalized via SuzukiMiyaura, Sonogashira and Stille cross-coupling reactions. The 2-position of the 2-butylthiooxazoles obtained was further coupled to various organozinc reagents through palladium-or nickel-mediated cross-coupling reactions.

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Cited by 21 publications
(12 citation statements)
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“…Derivatives of oxadiazole-2-tines are of undoubted interest in the search for new antibacterial drugs, since they contain a number of pharmacophore groups [14][15][16]. In this regard, in order to search for new anti-tuberculosis drugs and study the structure-activity relationship [17][18][19][20][21], we studied the interaction of acylglycine hydrazides with carbon disulfide in the presence of potassium hydroxide. Further acidification of the resulting potassium salt of dithiocarbamic acid with 0.1 N HCl solution leads to the formation of cyclic products -1,3,4-oxadiazole-2-thiones.…”
Section: Some Directions In the Modification Of Azolesmentioning
confidence: 99%
“…Derivatives of oxadiazole-2-tines are of undoubted interest in the search for new antibacterial drugs, since they contain a number of pharmacophore groups [14][15][16]. In this regard, in order to search for new anti-tuberculosis drugs and study the structure-activity relationship [17][18][19][20][21], we studied the interaction of acylglycine hydrazides with carbon disulfide in the presence of potassium hydroxide. Further acidification of the resulting potassium salt of dithiocarbamic acid with 0.1 N HCl solution leads to the formation of cyclic products -1,3,4-oxadiazole-2-thiones.…”
Section: Some Directions In the Modification Of Azolesmentioning
confidence: 99%
“…This is the case for coupling reactions with unsaturated thioethers [144,145,241] and with alkenylphosphates, if dppf is used as ligand [147]. Notably, however, as a result of their higher nucleophilic character, alkylzinc reagents show a lower propensity to favor 1,2-migration than arylzincs in their palladium-catalyzed reaction with alkenylphosphates using the ligand PPF-tBu (179) of the JosiPhos family [148].…”
Section: Cross-coupling With C(sp)-and C(sp 2 )-Electrophilesmentioning
confidence: 99%
“…Oxazoles are considered an important class of nitrogen heterocycles that exhibit diverse biological activities. A large number of oxazole‐containing natural products that exhibit anti‐cancer, antifungal, or antibacterial properties have been isolated, and many of these compounds have been synthesized . Because of the sheer number of biologically active oxazole natural products and pharmaceuticals that have emerged in the last 20 years, this class of compounds has begun to approach the forefront of important nitrogen heterocycles .…”
Section: Introductionmentioning
confidence: 99%