Regioselective synthesis of polyheterocycles from 4-cyclohex-2-enyl-3-hydroxy-1-methylquinolin-2(1H)-one

Article abstract of DOI:10.1080/00397919608003824

4-Cyclohex-2-enyl-3-hydroxy-1-methylquinolin-2(1H)-one (4) was prepared in 90% yield by the thermal [3,3]sigmatropic rearrangement of 3-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) in refluxing chlorobenzene for 10 h. Compound (4) was cyclised through a sequence of reactions viz. i) acetylation ii) addition of bromine and iii) treatment of the acetyl dibromo compound (6) with base to give a bicyclic product (7) in 90% yield. Treatment of compound 4 with pyridine hydrobromide perbromide in dichloromethane at 0-5°C afforded a cyclic product B in excellent yield. Compound 4 when treated with cold conc. sulphuric acid at 0-5°C furnished the bicyclic product 12 in 89% yield.

Full text of DOI:10.1080/00397919608003824

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Synthetic Communications: An
International Journal for Rapid
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Organic Chemistry
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Regioselective Synthesis of
Polyheterocycles From 4-
Cyclohex-2-ENYL-3-Hydroxy-1-
Methylquinolin-2(1H)-One
K. C. Majumdar a & A. K. Kundu a
a Department of Chemistry , University of Kalyani ,
Kalyani, 741 235, W.B, INDIA
Published online: 23 Aug 2006.
To cite this article: K. C. Majumdar & A. K. Kundu (1996) Regioselective Synthesis
of Polyheterocycles From 4-Cyclohex-2-ENYL-3-Hydroxy-1-Methylquinolin-2(1H)-One,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 26:21, 4023-4037, DOI: 10.1080/00397919608003824
To link to this article: http://dx.doi.org/10.1080/00397919608003824
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