N-Aryl Lactams by Regioselective Ozonation of N-Aryl Cyclic Amines | Zendy

Francesco Saliu | Zendy; Marco Orlandi | Zendy; Maurizio Bruschi | Zendy

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N-Aryl Lactams by Regioselective Ozonation of N-Aryl Cyclic Amines

Author(s) -

Francesco Saliu,

Marco Orlandi,

Maurizio Bruschi

Publication year - 2012

Publication title -

isrn organic chemistry

Language(s) - English

Resource type - Journals

eISSN - 2090-5157

pISSN - 2090-5149

DOI - 10.5402/2012/281642

Subject(s) - aryl , regioselectivity , ring (chemistry) , chemistry , cyclic amines , medicinal chemistry , organic chemistry , combinatorial chemistry , amine gas treating , catalysis , alkyl

Ozonation of N -aryl-cyclic amines in organic solvents gave N -aryl-lactams regioselectively. In particular, 4-(4-aminophenyl)-morpolin-3-one, a key intermediate in the preparation of factor Xa inhibitors, was obtained in fair yields. The method represents an alternative approach for the lactamization of tertiary N -arylic substrates and is based on a “metal-free” introduction of the carbonyl function into the heterocyclic ring.

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