A new heteropentacyclic system via coupling sterically crowded o-benzoquinone with o-phenylenediamines

Ivakhnenko, E. P.; Malay, Vasily; Демидов, О. П.; Knyazev, Pavel A.; Makarova, Nadezhda I.; Минкин, В. И.

doi:10.1039/d2ob02165j

Cited by 2 publications

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References 34 publications

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“…At the first stage, this reaction follows one of three possible reaction pathways, including Schiff base formation (attack at the C(3) center), Michael addition at C(1), or nucleophilic substitution (S N H) at the C(2) center [ 13 – 15 ]. Most readily used is the pathway involving carbonyl–amine condensation and Schiff base formation, which is then cyclized [ 12 , 16 ]. The reaction of 1 with arylamines 2a is performed in toluene solution in the presence of a catalytic amount of p -toluenesulfonic acid.…”

Section: Introductionmentioning

confidence: 99%

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

Ivakhnenko,

Malay,

Knyazev

et al. 2024

Beilstein J. Org. Chem.

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A convenient method for the synthesis of a series of 2-(arylamino)-3H-phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3H-phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 220–250 °C is described, and the compounds were characterized by means of single-crystal X-ray crystallography, NMR, UV–vis, and IR spectroscopy, as well as cyclic voltammetry. The reaction with o-amino-, o-hydroxy-, and o-mercapto-substituted arylamines widened the scope and provided an access to derivatives of N,O- and N,S-heteropentacyclic quinoxalinophenoxazine, triphenodioxazine and oxazinophenothiazine systems.

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