182890-79-5

Upstream product

• 172604-63-6 3-hydroxy-1-methylquinolin-2(1H)-one 
• 182890-78-4 3-(Cyclohex-2-enyloxy)-1-methyl-1H-quinolin-2-one 

Downstream Products

• 182890-81-9 Acetic acid 4-(2,3-dibromo-cyclohexyl)-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl ester 
• 94298-57-4 3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one 
• 182890-80-8 Acetic acid 4-cyclohex-2-enyl-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl ester 

Relevant academic research and scientific papers

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

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.