Volume : IV, Issue : IX, September - 2014

Condensation of Heteroaromatic Ketones with 2–Aminobenzophenones under MW Irradiation

Do Hun Lee, Jung Tai Hahn, Dai Ll Jung

Abstract :

We first carried out Friedlander condensation of various heteroaromatic ketones 2a~f with 2–aminobenzophenones 1a~e under MW irradiation. To explore the scope and limitations of this condensation reaction under the above–mentioned reaction conditions, we generated a mini–liary of quinolines. Acetylpyridines 2a~c 2–acetylfuran 2d, 2–acetylthiophene 2e, and 4–methylacetophenone 2f were condensed with 1a~e under the above–mentioned optimal reaction conditions. The results are summarized in Table 1. Condensation of 2a~f with 1a~e afforded quinolines in good yields (60.0~74.5%); in these reactions, dibenzo [b,f][1,5]diazocines 19a~d were isolated as the minor product. However, 6,12–diphenyldibenzo[b,f][1,5]diazocine 19a was the only product formed in low yield when 1a was reacted with 4–acetylmorpholine 2g, 3–acetyl–2–oxazolidinone 2h (an amide), and 4–acetylimidazole 2i (yield of the product obtained from 2g, 2h, and 2i was 34.0%, 42.0%, and 41.0%, respectively). The effect of MW irradiation on quinoline formation can be explained on the basis of MW activation effects caused by dipole–dipole interactions, mechanistic considerations, and the increase in the polarity of the system during the progress of the reaction.  

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Article: Download PDF   DOI : 10.36106/ijar  

Cite This Article:

Do-Hun Lee, Jung-tai Hahn, Dai-ll Jung Condensation of Heteroaromatic Ketones with 2-Aminobenzophenones under MW Irradiation Indian Journal of Applied Research, Vol.4, Issue.9 September 2014

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