1602-00-2Relevant articles and documents
Mesoporous manganese oxide catalyzed aerobic oxidative coupling of anilines to aromatic azo compounds
Dutta, Biswanath,Biswas, Sourav,Sharma, Vinit,Savage, Nancy Ortins,Alpay, S. Pamir,Suib, Steven L.
, p. 2171 - 2175 (2016)
Herein we introduce an environmentally friendly approach to the synthesis of symmetrical and asymmetrical aromatic azo compounds by using air as the sole oxidant under mild reaction conditions in the presence of cost-effective and reusable mesoporous manganese oxide materials.
COOPERATION OF ARYLIMINODIMAGNESIUM MOLECULES: DEOXYGENATION OF AZOXYARENES BY MONO- AND BIFUNCTIONAL REAGENTS IN COMPARISON WITH THAT BY PHOSPHORUS(III) REAGENTS
Okubo, Masao,Inatomi, Yoshito,Eguchi, Izumi,Nishida, Hiroshi,Gotoh, Seiji,Matsuo, Koji
, p. 18 - 23 (1994)
Reaction of aryliminodimagnesium with nitrobenzene (Ar1NO2) in tetrahydrofuran (THF) gives unsymmetrical (unsym) azoxybenzene, which is deoxygenated to give unsym-azobenzene.The reaction is utilized for the independent prepar
Synthesis, in vitro and in vivo anticancer activities of novel 4-substituted 1,2-bis(4-chlorophenyl)-pyrazolidine-3,5-dione derivatives
Zhang, Xu-Yao,Gu, Yi-Fei,Chen, Ting,Yang, Dong-Xiao,Wang, Xi-Xin,Jiang, Bai-Ling,Shao, Kun-Peng,Zhao, Wen,Wang, Cong,Wang, Jun-Wei,Zhang, Qiu-Rong,Liu, Hong-Min
, p. 1781 - 1786 (2015)
To develop potent and selective anticancer agents, a series of novel 4-substituted 1,2-bis(4-chlorophenyl)-pyrazolidine-3,5-dione derivatives were designed and synthesized. All the compounds were evaluated for their antiproliferative activities against a panel of four human cancer cell lines. Among them, compound 4u is the most potent, exhibiting IC50 values ranging from 5.1 to 10.1 μM. Flow cytometry and western blot analyses revealed that treatment of MGC-803 cells with compound 4u induces early cellular apoptosis via activation of caspases-9/3. Furthermore, compound 4u effectively reduced the tumor growth exhibited by human gastric cancer cells in vivo without obvious adverse side effects. Our findings indicate that compound 4u may serve as a lead compound to target solid tumors.
Synthesis and crystal structure of the silver complexes [PPh4]2[Ag4Cl4 (ClC6H4N3C6H4Cl)2], [Et4N][Ag2(tolyl-N5-tolyl)3] ·2THF and [(n-Bu)4N]3 [Ag3I6]and about the reaction of [Ag(ClC6H4N3C6H4Cl)]2 and [Ag(tolyl-N5-tolyl)] 2 with iodine
Barboza Da Silva, Carlos F.,Schwarz, Simon,Mestres, Montserrat Galceran,Straehle, Joachim
, p. 2231 - 2236 (2004)
The silver triazenido complex [PPh4]2[Ag 4Cl4-(ClC6H4N3C 6H4Cl)2] (1) is formed by the reaction of silver bis(p-chlorinephenyl)triazenide with [PPh4]Cl in THF. It crystallizes in the monoclinic space group C2/c with a = 2816.9(3), b = 946.67(7), c = 2552.4(3) pm, β = 90.22(1)° and Z = 4. In the centrosymmetric anion of 1 the four Ag atoms together with two Cl atoms form a distorted octahedron. The Ag atoms are in equatorial positions. They are bridged by two Cl atoms and two triazenido ligands. The reaction of [Et4N]Br with silver bis(p-tolyl)pentaazadienid in THF yields [Et4N][Ag 2(tolyl-N5-tolyl)3] (2a). An analogous compound, [(n-Bu)4N][Ag2(tolyl-N5-tolyl) 3] (2b) is obtained by the reaction of [(n-Bu)4N]I with silver bis(p-tolyl)pentaazadienid in THF, when a threefold excess of the pentaazadienid is used. If both educts are used in equal amounts then [(n-Bu)4N]3[Ag3I6] (3) is formed. 2a crystallizes as 2a×2THF in the triclinic space group P1 and a = 1303.6(3), b = 1471.3(4), c = 1811.6(2) pm, α = 98.51(2)°, β = 93.33(2)°, γ = 112.50(2)° and Z = 2. The two Ag atoms in the anions of 2a and 2b are bridged by three pentaazadienido ligands with their atoms N1 and N3. One of the Ag atoms is in addition coordinated by the atoms N5 of two of the ligands, resulting in different coordinations for the two Ag atoms in form of a trigonal planar for one and a distorted square pyramidal arrangement for the other. 3 forms orthorhombic crystals with the space group Pca21 and a = 1675.0(6), b = 1698.8(2), c = 2612.8(5) pm and Z = 4. The anion [Ag3I6]3- is built up by three AgI4 tetrahedra sharing common faces. The silver triazenido and pentaazadienido complexes, [Ag(ClC6H4N3C6H 4Cl]2 and [Ag(tolyl-N5-tolyl)]2 are oxidized by I2 to form the azo compounds [ClC6H 4N=NC6H4Cl] (4) and [tolyl-N=N-tolyl] (5) as well as N2.
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Ogata,Shimizu
, p. 635 (1979)
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Kobayashi et al.
, p. 2039 (1972)
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Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines
Ben-David, Yehoshoa,Das, Uttam Kumar,Diskin-Posner, Yael,Kar, Sayan,Milstein, David
supporting information, p. 3744 - 3749 (2021/07/09)
We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).
Single crystal MnOOH nanotubes for selective oxidative coupling of anilines to aromatic azo compounds
Cao, Fangxian,Li, Jiayuan,Qu, Yongquan,Zhang, Mingkai,Zhang, Sai,Zou, Yong
supporting information, p. 19692 - 19697 (2021/09/20)
Catalytic synthesis of aromatic azo compounds by oxidative coupling of anilines using molecular oxygen represents a facile, green and valuable process; however, such an economical process suffers from poor catalytic activity and selectivity. Herein, novel single crystal MnOOH nanotubes with abundant Mn3+sites and high oxygen defects were successfully synthesized. The catalyst exhibited high selectivity for oxidative coupling of anilines, achieving complete transformation into aromatic azo compounds under mild conditions, even at room temperature.
