54974-61-7Relevant academic research and scientific papers
Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi-Mumm and regiospecific quinazolinone rearrangements
Jaffett, Victor A.,Nerurkar, Alok,Cao, Xufeng,Guzei, Ilia A.,Golden, Jennifer E.
supporting information, p. 3118 - 3128 (2019/03/26)
An efficient four-step, six-transformation protocol was developed to afford bioactive N-alkyl- or N-arylamide (E)-arylamidines featuring strategic amidine C3 modifications which were inaccessible or low yielding by previous methods. This synthetic approac
Reactions of 1-Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects
Yusubov, Mekhman S.,Soldatova, Natalia S.,Postnikov, Pavel S.,Valiev, Rashid R.,Svitich, Dmitry Y.,Yusubova, Roza Y.,Yoshimura, Akira,Wirth, Thomas,Zhdankin, Viktor V.
, p. 640 - 647 (2018/02/14)
New substituted 1-arylbenziodoxolones were prepared and their reactivity with azide anion as a nucleophile was investigated. It was found that independent of the presence of substituents, all reactions of 1-arylbenziodoxolones proceed as nucleophilic substitution of the iodonium leaving group in the electron-deficient benziodoxolone benzene ring. The presence of bulky substituents in the ortho position of the aryl ring slows the reaction down, while the presence of a moderately electron-withdrawing bromine substituent in para position to the iodine atom in the benziodoxolone ring moderately increases the rate of substitution. The presence of a strongly electron-withdrawing nitro group in the para position to the iodine atom in the benziodoxolone ring dramatically increases the rate of substitution. These observations are in agreement with the electronic requirements for internal nucleophilic substitution in the benziodoxole ring. A quantum-chemical computational study of the possible reaction paths is in agreement with the observed effects of substituents on the reactivity of arylbenziodoxolones in this reaction.
Micellar Catalysis of Organic Reactions. XXVI SNAr Reactions of Azide Ions
Broxton, Trevor J.,Christie, John R.,Chung, Roland P.-T.
, p. 855 - 864 (2007/10/02)
The azidodehalogenation of a number of aromatic compounds has been studied in the presence of micelles of cetyltrimethylammonium bromide (ctab).The variation of the observed rate of reaction with ctab concentration has been treated by using the model of R
1H- and 2H-Indazoles by Thermal and Photolytic Decomposition of o-Azidobenzoic Acid and o-Azidobenzaldehyde Derivatives
Ardakani, Manouchehr Azadi,Smalley, Robert K.,Smith, Richard H.
, p. 2501 - 2506 (2007/10/02)
Ethyl o-azidobenzimidate (6) and o-azidobenzamidine (7) on thermolysis yield 3-ethoxy- (9; X=OEt) and 3-amino-1H-indazole (9; X=NH2), respectively.The former product is also obtained on irradiation of the imidate in methanol-tetrahydrofuran solution. 2-Aryl- and 2-heteroaryl-3-chloro-2H-indazoles have been prepared by the action of hot thionyl chloride on o-azidoanilides.The trichloro-2H-indazoles obtained by the action of phosphorus pentachloride on o-azidobenzanilide (12) and by the action of thionyl chloride on N-(o-azidobenzoyl)-2-aminopyridine have been identified as the 3,5,7-trichloro derivatives.The reductive dehalogenation, nitration, and reactivity of the halogen towards nucleophiles, of 3-chloro-2-phenyl-2H-indazole (19) are reported.A new practicable synthesis of o-azidobenzaldehyde (31; X=O) is described.Thermolysis of its phenylhydrazone and semicarbazone derivatives yields 2H-indazoles.
