Abstract
Microwave (MW) irradiation activated the reaction of dimedone with aniline or p-chloroaniline in formic acid to give the acridine derivatives 2a and 2 b, respectively, which can be derivatized as the bisoximes 3 and bisphenylhydrazone 4. However, under the same reaction conditions 2- aminopyridine gave the xanthene derivative 6 and not the expected acridine derivative 2c. When 2-aminopyridine was allowed to react under MW irradiation with dimedone in presence of benzaldehyde in ethanol it gave the bis(dimedonyl)methane derivative 10. Cyclization of 10 has been enhanced under MW irradiation to give the xanthene derivative 9 in improved yield and in less time than the conventional heating. The structures of products were confirmed from the analysis of their IR, 1 H-NMR and mass spectra. The antimicrobial activity has been investigated for compounds 3, 4, 6 and 10.
Highlights
Chemical and pharmaceutical industries are facing constraints regarding the environmental aspects and saving energy
A major concern to overcome such problems in organic synthesis has considered the use of microwave (MW) irradiation as a source of energy
Acridine derivatives have a wide spectrum of biological activities as antibacterial, antimalarial, anticancer and mutagenic properties, principally connected with their ability to inhibit the enzymes acting on nucleic acids[4]
Summary
Chemical and pharmaceutical industries are facing constraints regarding the environmental aspects and saving energy. A one step reaction of dimedone (1) with aniline or p-chloroaniline in formic acid to give the 10aryl-decahydroacridine derivatives6 2a,b required heating at 150 oC for 23 hours.
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