10531-78-9Relevant articles and documents
Cu-Catalyzed Direct C-P Bond Formation through Dehydrogenative Cross-Coupling Reactions between Azoles and Dialkyl Phosphites
Hore, Soumyadip,Srivastava, Abhijeet,Singh, Ravi P.
, p. 6868 - 6878 (2019)
A direct dehydrogenative cross-coupling of azoles [C(sp2)-H] with dialkyl phosphites [P(O)-H] to access 2-phosphonated azoles using Cu(I)/Cu(II) as catalyst and K2S2O8/di-tert-butylperoxide as oxidant has been achieved. A remarkable advantage over reported procedures includes that oxazoles, imidazoles, benz(ox/othi/imid)azoles, and indole are found to react under optimized reaction conditions to provide corresponding adducts in high yields. The mechanistic insight of cross-coupling was obtained by deuterium kinetic isotope effect studies.
Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites
Hou, Chaodong,Ren, Yunlai,Lang, Rui,Hu, Xiaoxue,Xia, Chungu,Li, Fuwei
, p. 5181 - 5183 (2012)
The first Pd-catalyzed direct phosphonation of azoles with dialkyl phosphites has been achieved without addition of base or acid. This method involves the oxidative cleavage of C-H and P(O)-H bonds and represents an atom-efficiency alternative to the classical phosphonation of Ar-X. A Pd II/PdIV mechanism has been studied and proposed.
Unsymmetrical Pincer N -Heterocyclic Carbene-Nitrogen-Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp2-H Arylation of Benzoxazoles
Li, Yaqiu,Yu, Xiaojun,Wang, Yangdiandian,Fu, Haiyan,Zheng, Xueli,Chen, Hua,Li, Ruixiang
, p. 979 - 988 (2018)
An unsymmetrical pincer N-heterocyclic carbene-nitrogen-phosphine (CNP) and its palladium complexes PdCl2(κ2-CP) (4) and [PdCl(κ3-CNP)]PF6 (5·PF6) were synthesized. NMR spectra disclosed that the transformation of complex 4 structure occurred in the solution. Further NMR experimental and single crystal structure analysis of complex 4 provided unequivocal and structural evidence for the formation of complex [PdCl(κ3-CNP)]Cl (5·Cl) in the solution of complex 4. The catalytic performance of palladium complexes 4 and 5·PF6 was investigated with the direct Csp2-H arylation of benzoxazoles with aryl bromides. Notably, aryl bromides could give up to 97% arylation products in the presence of 0.5% complex 4. For ortho-substituted substrates, the steric hindrance had a significant impact, but product yields could be improved remarkably by extending reaction time. This result implied the catalytic active species in this system was stable and kept in a long lifetime. The flexible backbone and unsymmetrical pincer structure with a flank N-heterocyclic carbine should be a feasible strategy to realize an efficient catalytic transformation. This simple catalyst system first realized the direct arylation of aryl bromides with a catalyst loading as low as 0.25% without excessive base and copper as assistant catalyst.
Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides
Gao, Feng,Kim, Byeong-Seon,Walsh, Patrick J.
, p. 10661 - 10664 (2014)
An efficient room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl bromides is presented. The Pd(OAc)2/ NiXantphos-based catalyst enables the introduction of various aryl and heteroaryl groups, via a deprotonative cross-coupling process (DCCP) in good to excellent yields (60-99%). This journal is the Partner Organisations 2014.
Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities
Komuraiah, Buduma,Ren, Yichang,Xue, Mingming,Cheng, Binbin,Liu, Jin,Liu, Yao,Chen, Jianjun
, p. 1109 - 1116 (2021/03/16)
A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.
Method for synthesizing benzoxazole through microwave radiation of benzamide compound in water phase
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Paragraph 0078, (2019/03/08)
The invention discloses a method for synthesizing benzoxazole through microwave radiation of a benzamide compound in a water phase. The benzamide compound is added into the water phase under the microwave condition to be subjected to a cyclization reaction for generating the benzoxazole under the alkali condition, and the method for preparing the benzoxazole is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applied to a large number of functional groups, the yield is high, the number of by-products is small, and the method is easy to operate, safe, low in cost and environmentally friendly. (Please see the specifications for the formula).
