- Acylamino-Directed Specific Sequential Difunctionalizations of Anilides via Metal-Free Relay Reactions for p-Oxygen and o-Nitrogen Incorporation
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Novel acylamino-directed relay disubstitutions realize the sequential difunctionalizations of anilides (1) under mild and metal-free conditions for the first time. This [bis(trifluoroacetoxy)iodo]benzene (PIFA) and BF3·Et2O promoted straightforward reaction produces a series of p-acetoxyl- or p-alkoxyl-o-nitro-N-arylamides (2), which are key scaffolds of various drugs, functional materials, and bioactive molecules. The flexibility with respect to the functional groups in these products affords this novel protocol excellent versatility for synthetic applications.
- Wan, Yameng,Zhang, Zhiguo,Ma, Nana,Bi, Jingjing,Zhang, Guisheng
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p. 780 - 791
(2019/01/24)
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- Silver-Catalyzed Chemo- and Regioselective Nitration of Anilides
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A new and efficient Ag-catalyzed method for the nitration of anilides by using sodium nitrite as a cheap and available NO2 source has been developed. This C–H functionalization reaction is ortho-selective, achieves moderate to high yields and shows excellent functional group tolerance. Furthermore, it provides a novel approach to ortho-nitrated anilides, which are very tricky to access with traditional methods.
- Kianmehr, Ebrahim,Nasab, Sepideh Bahrami
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p. 6447 - 6452
(2018/11/01)
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- Regioselective Green Electrochemical Approach to the Synthesis of Nitroacetaminophen Derivatives
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A regioselective green synthesis of nitroacetaminophen derivatives was carried out by electrochemical oxidation of acetaminophen, N-(2-hydroxyphenyl)acetamide, and 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nitrite ion as a nucleophile. The present work has led to the development of a reagentless green and facile electrochemical method for the synthesis of some nitroacetaminophen derivatives.
- Salahifar, Eslam,Nematollahi, Davood,Bayat, Mehdi,Mahyari, Amir,Amiri Rudbari, Hadi
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p. 4666 - 4669
(2015/10/12)
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- Mizoroki-heck reactions with 4-phenoldiazonium salts
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Significantly better yields were achieved in Mizoroki-Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation-diazotation- precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium-catalyzed C-C bond forming reactions was demonstrated for a one-flask-synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd-catalyzed steps in a one-flask sequence, without any exchange of solvents or isolation of intermediates.
- Schmidt, Bernd,Hoelter, Frank,Berger, Rene,Jessel, Soenke
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supporting information; experimental part
p. 2463 - 2473
(2010/12/25)
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- Reductive cyclization with baker's yeast of 4-alkyl-2-nitro-acetanilides to 6-alkylbenzimidazoles and 1-hydroxy-2-methyl-6-alkylbenzimidazoles
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Reduction of 4-substituted 2-nitroacetanilides by baker's yeast in acid media effected cyclization, resulting in the formation of n-substituted 2-methylbenzimidazoles and 6-substituted 1-hydroxy-2-methylbenzimidazole via the chemo- and regioselective reduction of the 2-nitro aromatic group to amine or hydroxylamine.
- Navarro-Ocana,Olguin,Luna,Jimenez-Estrada,Barzana
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p. 2754 - 2756
(2007/10/03)
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- Mild, efficient and selective nitration of anilides, non-activated and moderately activated aromatic compounds with ammonium molybdate and nitric acid as a new nitrating agent
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Ammonium molybdate [Mo(VI)] is operationally simple, environmentally safe and inexpensive reagent. Regioselective nitration of anilides, non-activated and moderately activated aromatic compounds could be afforded by employing ammonium molybdate and nitric acid as mild and effective nitrating agent. This procedure works efficiently under reflux conditions to prepare mononitroderivatives of anilides, non-activated and moderately activated aromatic compounds in good to excellent yield with high regioselectivity.
- Sana, Sariah,Rajanna,Ali, Mir Moazzam,Saiprakash
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- A New Synthetic Route to 6,7-Dichloro-5,8-quinoxalinedione and Synthesis of Its Derivatives
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6,7-Dichloro-5,8-quinoxalinedione (2), an analogue of Dichlone, was prepared from 4-aminophenol (3) in 27percent overall yield in 8 steps via chloroxidation of the sulfuric acid salt of 8-amino-5-quinoxalinol (9) as a key step.And two derivatives, 6-chloro-5-hydroxypyrazinophenazine (10) and pyridoimidazoquinoxaline-6,11-dione (11), were prepared by reaction of 2 with 1,2-phenylenediamine and 2-aminopyridine in 79percent and 46percent yields, respectively.
- Han, Gyoonhee,Shin, Kye Jung,Kim, Dong Chan,Yoo, Kyung Ho,Kim, Dong Jin,Park, Sang Woo
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p. 2495 - 2502
(2007/10/03)
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- A NEW NITRATION PRODUCT, 3-NITRO-4-ACETAMIDOPHENOL, OBTAINED FROM ACETAMINOPHEN WITH NITROUS ACID
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Treatment of acetaminophen with an excess sodium nitrite under mildly acidic to neutral conditions results in smooth formation of new 3-nitro-4-acetamidophenol via N-acetyl-p-benzoquinone imine as an oxidation intermediate, which is a well-known, widely e
- Matsuno, Takanobu,Matsukawa, Tomoko,Sakuma, Yoshiharu,Kunieda, Takehisa
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p. 1422 - 1423
(2007/10/02)
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