- Studies on sequential Claisen rearrangement: Charge-accelerated [3,3]-sigmatropic rearrangement leading to polyheterocycles
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A number of quinolone-annulated pentacycles have been regioselectively synthesized in 90-95% yields by sequential Claisen rearrangements. The second synthesis is anhydrous AlCl3-catalyzed charge-accelerated aromatic Claisen rearrangement of 1-aryloxymethy
- Majumdar,Saha,Debnath
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p. 3657 - 3665
(2008/03/13)
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- studies in sigmatropic rearrangement of 3-(4-aryloxy-but-2-ynyloxy)-1-methylquinolin-2-ones: Synthesis of 3h-pyrano[2,3-c]quinolin-5(6H)-ones and furo[2,3-c]quinol-in-4(5H)-ones
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3-(4-Aryloxybut-2-ynyloxy)-1-methylquinolin-2-ones (3), in refluxing chlorobenzene, gave 1-aryloxymethyl-6-methyl-3H-pyrano[2,3-c] quinolin-5(6H)-ones (4) and / or, 1-aryloxymethyl-2,5-dimethylfuro[2,3-c]quinolin-4(5H)-ones (5). The base or the radical initiator (azoisobutyronitrile) does not seem to have any effect on the formation of the products. Substrates (3) provided only products (5) in the presence of toluene-4-sulphonic acid. All the substrates (3) studied so far underwent sigmatropic rearrangements at the 4-quinolin-3-ynyloxypropynyl function of compound (3) to give products (4) and/or (5).
- Majumdar, Krishna C.,Kundu, Anup K.
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p. 1467 - 1475
(2007/10/03)
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