377725-39-8Relevant articles and documents
Oxidative Cleavage of C2-C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates
Kalbandhe, Amit H.,Kavale, Ashish C.,Thorat, Prerana B.,Karade, Nandkishor N.
supporting information, p. 763 - 768 (2016/03/12)
On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.
Effect of catalytic alkali metal bromide on Hofmann-type rearrangement of imides
Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
supporting information; experimental part, p. 8574 - 8576 (2012/09/07)
The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.
Effect of the amino versus the acylamino substituent on the product isomer distribution in the methanolysis of 5-(substituted)-2-[(methylsulfonyl)oxy]isoindole-1,3-diones
Kerrigan, John E,Vagnoni, Lisa M
, p. 8227 - 8235 (2007/10/03)
The effect of the NH2 versus the CH3CONH and PhCH2CONH substituents at the 5-position in 5-(substituted)-2-[(methylsulfonyl)oxy]isoindole-1,3-diones, on the product isomer distribution resulting from methanolysis, was investigated both experimentally and at the RHF/3-21G*, RHF/6-31+G* and B3LYP/6-31+G* levels of theory. The influence of solvent on the transition structure was investigated using the Onsager SCRF model. The influence of these substituents on the transition state (TS) leading to tetrahedral intermediate was studied. The 5-amino (para to C-1) function makes the C-1 carbonyl carbon more electron-rich and less reactive toward nucleophilic attack. A predominance of the isomer formed from initial nucleophilic attack at C-3 is observed for the NH2 substituent, whereas this selectivity is greatly reduced for the acylamino substituents. Examination of the LUMO from ab initio calculations performed on the starting materials at the RHF/6-31G* level give a good qualitative description of the regioselectivity observed from experiment. Calculated ΔEa values of this initial reaction step give a qualitative description of the experimentally observed regioselectivity in agreement with the LUMO model and resonance argument.