- Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
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In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi
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supporting information
p. 5905 - 5911
(2021/07/12)
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- Preparation method of 2-methyl phenylhydrazine sulfate
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The invention relates to a preparation method of 2-methyl phenylhydrazine sulfate. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. In the diazotization and reduction steps, reaction liquid is kept with high acidity by means of concentrated hydrochloric acid, so that the reaction is smoothly and fully carried out. In the reduction step, zinc powder-concentrated hydrochloric acid is taken as a reducing agent to replace sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric and the like, the reducing property isgood, the yield is high, the reaction time is shortened, impurities such as zinc hydroxide generated by the reaction are conveniently removed, and the product is few in impurity and high in purity. In the salt formation step, acetone is used to wash, so that the purity of the product is improved, and the appearance of the product is ensured. According to the preparation method, the process is stable and reliable, the operation is easy, the product purity is high (the content of the product detected by high performance liquid chromatography is greater than or equal to 99.1%), the yield is greater than or equal to 42%, and the demand on 2-methyl phenylhydrazine sulfate in the market is fully met.
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Paragraph 0037; 0039-0044
(2018/07/30)
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- Preparation method of 2-methyl phenylhydrazine phosphate
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The invention relates to a preparation method of 2-methyl phenylhydrazine phosphate. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. Inthe diazotization and reduction steps, reaction liquid is kept with high acidity by means of concentrated hydrochloric acid, so that the reaction is smoothly and fully carried out. In the reduction step, zinc powder-concentrated hydrochloric acid is taken as a reducing agent to replace sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric and the like, the reducing propertyis good, the yield is high, the reaction time is shortened, impurities such as zinc hydroxide generated by the reaction are conveniently removed, and the product is few in impurity and high in purity.In the salt formation step, acetone is used to wash, so that the purity of the product is improved, and the appearance of the product is ensured. According to the preparation method, the process is stable and reliable, the operation is easy, the product purity is high (the content of the product detected by high performance liquid chromatography is greater than or equal to 99.2%), the yield is greater than or equal to 42%, and the demand on 2-methyl phenylhydrazine phosphate in the market is fully met.
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Paragraph 0020; 0022; 0024; 0030; 0032; 0034; 0037-0044
(2018/07/30)
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- Preparation method of 2-methyl phenylhydrazine hydrochloride
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The invention relates to a preparation method of 2-methyl phenylhydrazine hydrochloride. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. In the diazotization and reduction steps, reaction liquid is kept with high acidity by means of concentrated hydrochloric acid, so that the reaction is smoothly and fully carried out. In the reduction step, zinc powder-concentrated hydrochloric acid is taken as a reducing agent to replace sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric and the like, the reducing property is good, the yield is high, the reaction time is shortened, impurities such as zinc hydroxide generated by the reaction are conveniently removed, and the product is few in impurity and high in purity. In the salt formation step, acetone is used to wash, so that the purity of the product is improved, and the appearance of the product is ensured. According to the preparation method, the processis stable and reliable, the operation is easy, the product purity is high (the content of the product detected by high performance liquid chromatography is greater than or equal to 99%), the yield isgreater than or equal to 39%, and the demand on 2-methyl phenylhydrazine hydrochloride in the market is fully met.
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Paragraph 0020; 0022; 024; 0027-0034; 0040; 0042; 0044
(2018/07/30)
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- Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid
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N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone.
- Maclean, Mark A.,Diez-Cecilia, Elena,Lavery, Christopher B.,Reed, Mark A.,Wang, Yanfei,Weaver, Donald F.,Stradiotto, Mark
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supporting information
p. 100 - 104
(2015/12/18)
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- Remazol-Catalyzed Hydroperoxyarylation of Styrenes
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A mild photocatalytic hydroperoxyarylation of styrenes has been developed, in which a novel photocatalyst, remazol brilliant blue R (RBBR), is employed at low catalytic loading (1 mol%). The operationally easy procedure uses air as the dioxygen source. Simple mono-substituted styrenes react with aryl hydrazines in moderate-to-good yields. RBBR is proposed to act as a photosensitizer for the generation of singlet oxygen.
- Chen, Ying-Ho,Lee, Ming,Lin, Yi-Zhen,Leow, Dasheng
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supporting information
p. 1618 - 1621
(2015/08/06)
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- Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400
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An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.
- Chen, Junmin,Zhang, Yimin,Hao, Wenyan,Zhang, Rongli,Yi, Fei
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p. 613 - 617
(2013/07/25)
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- Antiimplantation Agents: Part I - 1-Arylthiosemicarbazides
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Several 1-arylthiosemicarbazides, 2-arylhydrazinothiazolines and 2-arylhydrazinodihydrothiazines have been examined for their antiimplantation activity in rats.Among the active compounds, 4-methyl-1-(3,5-bistrifluoromethylphenyl)thiosemicarbazide (3, C 2696-Go) and the corresponding 4,4-dimethyl (47), ethyl (4), n-butyl (5) and allyl (6) derivatives completely inhibit implantation at doses 10, 3, 20, 20 and 30 mg/kg respectively.The 3,4-dichlorophenyl analogue (32) is effective at a dose of 30 mg/kg. 2-(3,5-Bistrifluoromethylphenyl)hydrazinothiazoline (51) and the corresponding dihydrothiazine (63) show a weaker activity.The biological profile of C 2696-Go has been investigated in detail.It appears to prevent implantation by its antiuterotropic activity and ability to inhibit desiduoma formation.
- Nagarajan, K.,Talwalker, P.K.,Kulkarni, C.L.,Venkateswarlu, A.,Prabhu, S.S.,Nayak, G.V.
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p. 1243 - 1257
(2007/10/02)
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