77326-36-4Relevant academic research and scientific papers
Preparation method of 2,6-dibromoaniline
-
Paragraph 0018; 0026, (2020/08/27)
The invention discloses a preparation method of 2,6-dibromoaniline. According to the method, 2,6-difluorobenzonitrile is used as an initial raw material, and the 2,6-dibromoaniline is synthesized through six steps of reactions including ammonolysis, diazotization bromination, re-ammonolysis, re-diazotization bromination, amidation and Hofmann degradation. The 2,6-dibromoaniline obtained in the process is a brown solid, and the purity of the 2,6-dibromoaniline is 98% or above.
"Nanorust"-catalyzed benign oxidation of amines for selective synthesis of nitriles
Jagadeesh, Rajenahally V.,Junge, Henrik,Beller, Matthias
, p. 92 - 96 (2015/02/19)
Organic nitriles constitute key precursors and central intermediates in organic synthesis. In addition, nitriles represent a versatile motif found in numerous medicinally and biologically important compounds. Generally, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. Herein, we report the selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable "nanorust" (nanoscale Fe2O3)-based catalysts applying molecular oxygen.
Changes in the activity and selectivity of herbicides by selective fluorine substitution, taking bentranil and classic analogues as examples
Hamprecht, Gerhard,Wuerzer, Bruno,Witschel, Matthias
, p. 117 - 122 (2007/10/03)
The introduction of fluorine atoms into 2-phenyl-4H-3,1-benzoxazin-4-one (bentranil) led to sweeping changes in its herbicidal properties in some cases, and 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one ('fluorobentranil') was found to be the most active compound. It can be prepared from 2-amino-6-fluoro-benzoic acid or by direct halogen exchange of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one. The latter reaction was investigated on a pilot scale, including a high-temperature (350°C) potassium fluoride halogen exchange without solvent. When sulfolane was used as a solvent, a side reaction at 220°C - partial decomposition to a diphenylether - could be prevented by addition of a small amount of a radical scavenger. Other intermediates with a pseudohalogen substitution were obtained by side-chain chlorination of suitable methylsulfanyl benzoic acid precursors and halogen exchange. 'Fluorobentranil' shows good broad-leaf activity and selectivity on rice, cereals and maize. In a second case study, the fluoro-substituted anthranilic acids mentioned above were also found to be appropriate for synthesizing herbicidal sulfonylurea (SU) compounds via Meerwein reaction of their aniline function. Methyl 2-[({[(4-chloro-6-methoxy-2- pyrimidinyl)-amino]carbonyl}amino)sulfonyl]-6-fluorobenzoate is an example of a SU that is compatible with maize, whereas the unsubstituted Classic analogue is not selective.
IMIDAZO-PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS
-
Page 57, (2010/02/04)
A class of 8-fluoro-3-phenylimidazo[1,2-a]pyridine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group, or by a pyrrolidinonyl group, which is directly attached or bridged by an oxygen atom or by a -NH- or -OCH2- linkage, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.
Ambident Behavior of Ketone Enolate Anions in SNAr Substitutions on Fluorobenzonitrile Substrates
Guedira, Nour-Eddine,Beugelmans, Rene
, p. 5577 - 5585 (2007/10/02)
2,6-Difluorobenzonitrile was found to be a suitable substrate for studying carbon versus oxygen nucleophilic attack by enolate anions of weakly acidic ketones.The influence of the nucleophile structure and the solvent are investigated.The charge control character of the reaction and the influence of the substrate are discussed.
EXLUSIVE ORTHO CYANATION AND ALKYLTHIOCARBONYLATION OF ANILINES AND PHENOLS USING BORON TRICHLORIDE
Adachi, Makoto,Sugasawa, Tsutomu
, p. 71 - 84 (2007/10/02)
Use of boron trichloride with or without an aditional Lewis acid makes possible a one-step synthesis of 2-cyano and 2-alkylthiocarbonyl anilines and phenols.
Direct Synthesis of 2,4-Diaminoquinazolines from 2-Fluorobenzonitriles
Hynes, John B.,Pathak, Alpana,Panos, Constantina H.,Okeke, Claudia C.
, p. 1173 - 1177 (2007/10/02)
In a search for new methods for preparing 2,4-diaminoquinazolines having a diversity of substituents in the benzenoid ring, it was found that the reaction of 2,6-difluorbenzonitrile with guanidine carbonate gave 2,4-diamino-5-fluoroquinazoline in excellent yield.Extension of this approach to other 2-fluorobenzonitriles, some of which were elaborated for the first time, showed that this reaction possesses considerable generality.The cyclization was sucessful even when electron donating groups were present at position six.Only in two cases where a primary or secondary amino group was also present ortho to the cyano group was this transformation unsucessful.
Process for the production of 2,6-diaminobenzonitrile derivatives
-
, (2008/06/13)
2,6-Diaminobenzonitriles, useful in the production of N-(2-cyano-3-substituted or unsubstituted amino-phenyl)oxamate and N-(2-cyano-3-substituted or unsubstituted amino-phenyl)tetrazole-5-carboxamide antiallergy and antisecretory agents, are prepared by sequential displacement of the fluoro substituents from 2,6-difluorobenzonitrile with the appropriately substituted amine.
Preparation of fluorinated anthranilic acid and anthranilonitrile
-
, (2008/06/13)
Fluorinated anthranilic acid and anthranilonitrile, and a novel process for their preparation by reacting 2,6-difluorobenzonitrile with ammonia and, if the acid is required, hydrolyzing the resulting 6-fluoroanthranilonitrile with a basic compound. The two novel end products are valuable intermediates for the preparation of compounds which are useful for controlling various animal pests and plant pests.
N-(Aminophenyl)oxamic Acids and Esters as Potent, Orally Active Antiallergy Agents
Klaubert, Dieter H.,Sellstedt, John H.,Guinosso, Charles J.,Capetola, Robert J.,Bell, Stanley C.
, p. 742 - 748 (2007/10/02)
A series of N-(2-cyano-substituted-phenyl)oxamates was prepared by acylation of the appropriate anthranilonitrile with ethyloxalyl chloride.Hydrolysis with sodium hydroxide gave the corresponding oxamic acid sodium salts.These compounds were extremely potent when tested in the rat passive cutaneous anaphylaxis (PCA assay either by the ip or the po route of administration).One of the sodium salts, oxoacetic acid sodium salt (11a, Wy-41 195), has ED50 value of 0.07 mg/kg po and has been selected for further evaluation.
