Studies in [3, 3] Sigmatropic Rearrangement: Regioselective Cyclization of 5-(Cyclohex-2-Enyl)-6-Hydroxy-1-Methylquinolin-2(1H)-One |
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| Authors: | K. C. Majumdar P. Biswas S. K. Ghosh |
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| Affiliation: | 1. Department of Chemistry , University of Kalyani , Kalyani, 741 235, West Bengal, India;2. Department of Chemistry , University of Kalyani , Kalyani, 741 235, West Bengal, India;3. Department of Chemistry , Chakdaha College , W.B., India |
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| Abstract: | Thermal [3,3] sigmatropic rearrangement of 6-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) afforded 5-cyclohex-2-enyl-6-hydroxy-l-methyl-quinolin-2(1H)-one (4) in 86% yield. Compound 4 on treatment with pyridine hydrotribromide in CH2Cl2 gave exclusively non-bridged product 6 (85%) whereas compound 4 by a different route viz., acetylation followed by bromine addition and cyclization gave the bicyclic product 7 (80%). Compound 4 also furnished a bicyclic product 11 (80%) on treatment with cone. H2SO4. |
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