Abstract
An efficient one-pot synthesis of 4-amino-3, 4-dihydroquinolin-2-ones from 3-(2-nitrophenyl)-1, 4-disubstituted azetidin-2-ones is described. Microwave assisted transfer hydrogenation of a nitro group followed by in situ β-lactam ring opening by the newly formed amino group is the key step in this synthesis.
Highlights
Apart from the substructure of widely used antibiotics[1,2,3] such as penicillin, cephalosporins, monobactams etc., the azetidin-2-one (β-lactam) skeleton has been recognized as a useful building block in stereoselective syntheses of biologically important compounds.[4]
The strain energy associated with the four membered azetidin-2-one ring makes it susceptible for nucleophilic ring cleavage
In continuation of our efforts towards the synthesis of substituted β-lactams via the Staudinger reaction[14] and their utility as synthons[15] for the synthesis of various biologically important compounds, we report a rapid and practical synthesis of 4-amino-3, 4-dihydroquinolin-2ones from 1,3-disubstituted-4-(2-nitrophenyl)azetidin-2-ones via reduction of the nitro group followed by the intramolecular nucleophilic opening of the azetidin-2-one ring
Summary
Apart from the substructure of widely used antibiotics[1,2,3] such as penicillin, cephalosporins, monobactams etc., the azetidin-2-one (β-lactam) skeleton has been recognized as a useful building block in stereoselective syntheses of biologically important compounds.[4].
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