1157-94-4Relevant academic research and scientific papers
3, 5-disubstituted isoxazole derivative and synthesis method thereof
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Paragraph 0011; 0023; 0036, (2021/08/14)
The invention provides a 3, 5-disubstituted isoxazole derivative and a synthesis method thereof, and belongs to the technical field of organic synthesis medicines and medical intermediates. The method comprises the following steps: adding a proper solvent
General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies
Fernandes, Alessandra A. G.,da Silva, Amanda F.,Okada, Celso Y.,Suzukawa, Vitor,Cormanich, Rodrigo A.,Jurberg, Igor D.
, p. 3022 - 3034 (2019/05/17)
A general platform for the conversion of isoxazol-5-ones to 3,5-disubstituted isoxazoles has been developed via a two-step strategy. The first step leads to the formation of 5-(pseudo)halogenated isoxazoles, while in the second, a variety of heteroalkyl-, heteroaryl-, alkyl-, alkenyl-, alkynyl- and aryl-chains can be installed via nucleophilic substitutions or palladium catalyzed cross-coupling reactions.
Copper-catalyzed aerobic oxidative C-O bond formation for the synthesis of 3,5-disubstituted isoxazoles from enone oximes
Sun, Yadong,Abdukader, Ablimit,Zhang, Haiyan,Yang, Wanle,Liu, Chenjiang
, p. 55786 - 55789 (2017/12/26)
A direct access to 3,5-disubstituted isoxazoles has been accomplished through an intramolecular oxidative coupling reaction of enone oximes using a catalytic quantity of Cu(OAc)2. This method features an inexpensive metal catalyst, molecular ox
A direct access to isoxazoles from ynones using trimethylsilyl azide as amino surrogate under metal/catalyst free conditions
Kumar, Gadi Ranjith,Kumar, Yalla Kiran,Reddy, Maddi Sridhar
supporting information, p. 6589 - 6592 (2016/06/01)
A general method for isoxazoles from readily available ynones using trimethylsilyl azide as an amino surrogate, likely via an unprecedented hydroazidation of the alkyne and denitrogenative cyclization, is demonstrated. The method neither required any cata
Cyclocondensation of hydroxylamine with 1,3-bis(het)arylmonothio 1,3-diketones and 1,3-bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity
Raghava, Byregowda,Parameshwarappa, Gangajji,Acharya, Anand,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.,Ila, Hiriyakkanavar
, p. 1882 - 1892 (2014/04/03)
Efficient routes for the regioselective synthesis of 3,5-bis(het) arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine hydrochloride with either 1,3-bis(het)aryl-monothio-substituted 1,3-diketones 1 or with 3-methylthio-1,3-bis(het)aryl-2-propenones 2 under various reaction conditions. In the first protocol, diketones 1 were treated with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene to give 3,5-bis(het)arylisoxazoles 5, in which the het(aryl) moiety attached to thiocarbonyl group of the monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het) arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors 1 and 2 has been suggested.
Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity
Raghava, Byregowda,Parameshwarappa, Gangajji,Acharya, Anand,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.,Ila, Hiriyakkanavar
, p. 1882 - 1892 (2015/10/05)
Efficient routes for the regioselective synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine hydrochloride with either 1,3-bis(het)aryl-monothio-substituted 1,3-diketones 1 or with 3-methylthio-1,3-bis(het)aryl-2-propenones 2 under various reaction conditions. In the first protocol, diketones 1 were treated with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene to give 3,5-bis(het)arylisoxazoles 5, in which the het(aryl) moiety attached to thiocarbonyl group of the monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het)arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors 1 and 2 has been suggested.
