134935-86-7Relevant academic research and scientific papers
Solid-phase organic synthesis of methyl isoxazole-5-carboxylates based on wang resin-bound 1-phenylselenoacrylate
Tang, Ni,Sheng, Shou-Ri,Hu, Qiao-Sheng,Qu, Hong-En,Cai, Ming-Zhong
experimental part, p. 3279 - 3287 (2012/09/08)
A novel Wang resin-bound 1-phenylselenoacrylate reagent has been developed and used as dipolarophile for the 1,3-dipolar cycloaddition with nitrile oxides to the regioselective synthesis of methyl 3-substituted isoxazole-5-carboxylates in good yields and
Methyl 3-Substituted-isoxazole-5- Carboxylates syntheses on solid supports via wang resin-bound 2,3-dibromopropionate
Sheng, Shou-Ri,He, Ai-Ying,Wei, Mei-Hong,Zhu, Ai-Li,Cai, Ming-Zhong
, p. 444 - 448 (2012/10/29)
A novel Wang resin-bound 2,3-dibromopropionate reagent has been developed and used as a potential dipolarophile for the facile preparation of methyl 3-substituted-isoxazole-5-carboxylates through triethylamine, promoting a sequence of reactions involving the in situ generation of 2-bromoacrylate resin and nitrile oxide, regioselective 1,3-dipolar cycloaddition, and loss of hydrogen bromide in one pot, and then cleavage from the resin with sodium methoxide. The advantages of this method include simple operation and mild conditions with good yield and high purity of the products. Copyright
Efficient synthesis and utilization of phenyl-substituted heteroaromatic carboxylic acids as aryl diketo acid isosteres in the design of novel HIV-1 integrase inhibitors
Zeng, Li-Fan,Zhang, Hu-Shan,Wang, Yun-Hua,Sanchez, Tino,Zheng, Yong-Tang,Neamati, Nouri,Long, Ya-Qiu
scheme or table, p. 4521 - 4524 (2009/04/08)
Three new types of aryl diketo acid (ADK) isosteres were designed by conversion of the biologically labile 1,3-diketo unit into heteroaromatic motif such as isoxazole, isothiazole, or 1H-pyrazole to improve the physicochemical property of ADK-based HIV-1 integrase (IN) inhibitors. The synthesis of the heteroaromatic carboxylic acids was established by employing phenyl β-diketoester or benzaldehyde as the starting material and 1,3-dipolar cycloaddition as the key reaction. Of the compounds tested, the 3-benzyloxyphenyl-substituted isoxazole carboxylic acid displayed the best IN inhibitory and antiviral activities, with N-hydroxylamidation enhancing the in vitro and in vivo potency. These findings are important for further optimization of ADK-based IN inhibitors.
DFT-HSAB prediction of regioselectivity in 1,3-dipolar cycloadditions: Behavior of (4-substituted)benzonitrile oxides towards methyl propiolate
Ponti, Alessandro,Molteni, Giorgio
, p. 1156 - 1161 (2007/10/03)
The regioselectivity of 1.3-di-polar cycloadditions between (4-substituted)benzonitrile oxides and methyl propiolate cannot be rationalized on the basis of the electron demand of the reactants or frontier molecular-orbital theory. To this problem, we have
