73902-63-3Relevant academic research and scientific papers
Copper-mediated regioselective efficient direct ortho-nitration of anilide derivatives
Reddy Depa, Manmohan,Potla, Suneetha,Narkhede, Umesh C.,Jadhav, Vinod D.,Vidavalur, Siddaiah
supporting information, (2020/07/20)
The mild and readily available Cu(NO3)2 mediated ortho nitration of anilides with broad substrate using K2S2O8 as an oxidant in the absence of any other metal catalyst and nitrating agent under mild conditions was reported for the first time.
Atropisomeric and conformational properties of 6N-benzoyl-and 6N-p-tosyl-1,6-benzodiazocines: Comparison with those of 1,5-benzodiazepines
Tabata, Hidetsugu,Murai, Kazuya,Funaki, Kaoru,Takemae, Chihiro,Tasaka, Tomohiko,Oshitari, Tetsuta,Takahashi, Hideyo,Natsugari, Hideaki
, p. 566 - 581 (2019/08/01)
The atropisomeric and conformational properties of the eight-membered 1,6-benzodiazocines (2) with 6N-benzoyl (A) and 6N-p-tosyl (B) groups were examined by comparing them with those of the seven-membered 1,5-benzodiazepine congeners (1) (A, B). The confo
Copper-catalyzed mild nitration of protected anilines
Hernando, Elier,Castillo, Rafael R.,Rodríguez, Nuria,G?mez Arrayás, Ram?n,Carretero, Juan C.
supporting information, p. 13854 - 13859 (2016/02/18)
A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.
Design, anticonvulsive and neurotoxic properties of retrobenzamides / N- (nitrophenyl)benzamides and N-(aminophenyl)benzamides
Bourhim, Mustapha,Poupaert, Jacques H.,Stables, James P.,Vallee, Louis,Vamecq, Joseph
, p. 81 - 87 (2007/10/03)
Design, anticonvulsant properties in maximal electroshock-reduced seizures [MES] and seizures reduced by subcutaneous administration of pentetrazole (scPtz), and neurotoxicity of retrobenzamides (N- (nitrophenyl)benzamides and N-(aminophenyl) benzamides are reported. These data are further compared with those on carbamazepine, phenytoin, ameltolide and other reference compounds. Studies on retrobenzamides in mice dosed intraperitoneally point out a good anticonvulsant potential in the MES test for the amino derivatives (N-(aminophenyl)benzamides) and moderate activity for corresponding 'nitro' derivatives. In rats dosed orally, aminoretrobenzamides were, however, less active in the MES test than in mice dosed intraperitoneally. Differences between experimental animal species and administration routes lead to hypothesize rapid metabolization of compounds, reduced intestinal resorption and increased removal from body. The presence of a methyl substitution on the N-phenyl moiety of aminoretrobenzamides attenuated these discrepancies between mice and rats. Present results indicate that pharmacological values - including the dose offering anticonvulsant protection in 50 % of tested animals (ED50) and protective indices - obtained on some retrobenzamides may compete with phenytoin and carbamazepine values. By contrast with phenytoin, some retrobenzamides further exhibit activity in the scPtz test.
Reaction of N-Aryl- and N-Alkyl-benzimidoyl Chlorides with Silver Nitrate
Iley, Jim,Carvalho, Emilia,Norberto, Fatima,Rosa, Eduarda
, p. 281 - 290 (2007/10/02)
N-Arylbenzimidoyl chlorides, in which the N-aryl group is unsubstituted at the ortho- and para-positions, react with AgNO3 to yield N-(nitroaryl)benzamides, in which the NO2 group resides in the ortho- or para-position.N-Arylbenzimidoyl chlorides, in which the N-aryl ring is 2,4,6-trisubstituted, react with AgNO3 to yield the corresponding N-aryl-N-nitrobenzamides.The formation of both types of product can be explained by the intermediacy of an O-nitro imidate.Spectroscopic and chemical evidence is presented for the formation of this intermediate in the reaction of N-(2,4,6-trisubstituted phenyl)benzimidoyl chlorides with AgNO3.Rearrangement of the O-nitro imidate is unimolecular and intramolecular.The rate of rearrangement is independent of the substituent in the C-aryl ring, but increases with the electon-withdrawing ability of the substituents in the N-aryl ring.A mechanism is proposed in which the imidoyl chloride reacts with AgNO3 to produce first a nitrilium ion which goes on to form an O-nitro imidate that subsequently rearranges via a homolytic cleavage of the O-NO2 bond.The ortho:para ratios of N-(nitroaryl)benzamides obtained in the present work indicate that O-nitro imidates are not responsible for the high 1/2ortho:para ratios sometimes observed in the nitration of anilides.N-Alkylbenzimidoyl chlorides react with AgNO3 to form the corresponding N-nitro- and N-nitrosobenzamides.The mechanism of formation of the N-alkyl-N-nitrobenzamide arises from a pathway analogous to that for N-aryl-N-nitrobenzamides, involving a nitrilium ion that gives rise to an O-nitro imidate.The evidence for the formation of the N-nitrosobenzamide points to an alternative reaction of the imidoyl chloride with AgNO3.One possible mechanism for this reaction is described.
