24400-58-6Relevant academic research and scientific papers
Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines
Garia, Alankrita,Grover, Jatin,Jain, Nidhi
, p. 4125 - 4131 (2021/08/24)
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
Pyrolysis of Aryl Azides. VIII. Hammett Correlations of Rates of Pyrolysis of Substituted 2-Azidobenzophenones
Dyall, Leonard K.,Karpa, Gary J.
, p. 1231 - 1241 (2007/10/02)
Eight 2-azidobenzophenones with 4- or 5-substituents have been pyrolysed in decalin solution to yield 3-phenyl-2,1-benzisoxazoles.Rate values at 100 deg are correlated with the Hammett substituent constants, with respect to both the azido (A) and benzoyl (B) reaction centres, and yield the eqation log k = -4.38 + 2.08?-A -1.52?B.There is a similar equation for rates measured at 120 deg.Although nitro and benzoyl differ considerably in their neighbouring group abilitites in azide pyrolyses, it is concluded that they exert their effects through the same mechanism.The results are consistent with both published variants of an electrocyclic mechanism (Dyall; Smith, Budde and Chou).
REACTIONS OF ORGANIC ANIONS. PART XCVII. CLEAVAGE OF SUBSTITUTED α-(p- AND o-NITROPHENYL)-DEOXYBENZOINS BY SODIUM METHOXIDE IN METHANOL. DISPROPORTIONATION AND INTRAMOLECULAR CYCLIZATION REACTIONS OF NITRODIPHENYLMETHANE ANIONS
Jawdosiuk, Mikolaj,Kmiotek-Skarzynska, Irena,Czarnecka, Ewa
, p. 379 - 385 (2007/10/02)
Cleavage of substituted α-(p- and o-nitrophenyl) deoxybenzoins by sodium methoxide in methanol and subsequent transformations of resulting p- and o-nitrophenylphenylmethane anions have been investigated.
Organic photochemical reactions-V. Photorearrangement of anthranils into azepines
Ogata,Matsumoto,Kano
, p. 5205 - 5215 (2007/10/07)
The photolysis of anthranils (III) led to ring enlargement with the formation of 3-acyl-2-methoxy-3H-azepines (IV). The reaction in ether containing water or amines yielded the corresponding 2-oxo- or 2-amino-3H-azepines (V or VII). On the other hand, photolysis of some 7-substituted 3-phenylanthranils (IX and XIII) gave the corresponding 9-acridanone derivatives (X and XIV). A hypothetical scheme (anthranil → nitrene → azirene → azepine) similar to that proposed by Huisgen and Appl for the analogous ring enlargement of phenylazide is applicable to the anthranil rearrangement. By UV and IR spectroscopic methods, the last step was proved to involve a dark reaction of an intermediate (probably azirene species) with protic solvents.
