Monatshefte für Chemie/Chemical Monthly

Regioselective Heterocyclization of 3-(Cyclohex-2′-enyl)-4-hydroxy-6-methylpyran-2-one

KC Majumdar, S Ghosh

Index: Majumdar, Krishna C.; Ghosh, Subhojit Monatshefte fur Chemie, 2002 , vol. 133, # 10 p. 1317 - 1323

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Citation Number: 7

Abstract

Summary. Regioselective heterocyclization of 3-(cyclohex-2′-enyl)-4-hydroxy-6-methyl pyran-2-one with various reagents afforded different heterocycles. With N-iodosuccinimide in acetonitrile at 0–5° C it gave 6-methyl-9′-iodo-2′-oxabicyclo [3.3. 1] nonano [3, 2-c] pyran-2-one, with C 5 H 5 NHBr 3 or C 6 H 12 N 4 HBr 3 in CHCl 3 at 0–5° C it furnished 6- methyl-9′-bromo-2′-oxabicyclo [3.3. 1] nonano [3, 2-c] pyran-2-one. Cold concentrated ...