Abstract
Background: 1,3-Aminooxygenated functional groups exhibit a variety of biological and pharmacological activities including nucleosides, antibiotics and HIV protease inhibitors. On the other hand, carbazole-containing molecules show antiviral, antimalarial and antitumor activity. However, to the best of our knowledge there are no reports available on the synthesis of amidoalkyl carbazolols. In this connection, we wish to report the synthesis of amidoalkyl carbazolol derivatives by one-pot threecomponent reaction.
Methods: The synthetic one-pot three-component reaction of 4-hydroxycarbazole, different substituted aromatic aldehydes and amides was carried out under microwave-assisted heating conditions. The structures of obtained 1-amidoalkyl-2-carbazolol derivatives were confirmed by IR, NMR and mass spectra. Results: Various aromatic aldehydes such as fluoro-, nitro-, dimethoxy-, trimethoxy-derivatives reacted smoothly with 4-hydroxycarbazole and acetamide to give the corresponding amidoalkyl carbazolol derivatives in good yields (69-84%). Furthermore, the optimized reaction conditions worked well with benzamide with several benzaldehydes. Conclusion: We have developed the catalyst-free procedure for the one-pot three-component reaction of 4-hydroxycarbazole with aromatic aldehydes and acetamide/benzamide under MW conditions. Catalyst free, simple reaction conditions, good yields and environmentally benign procedure are the advantage of this protocol.Keywords: Hydroxycarbazole, 1-amidoalkyl-2-carbazolol derivatives, microwave irradiation, three-component reaction, orthoquinone methide.
Graphical Abstract
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