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A novel route to 6-substituted and 5,6-disubstituted 2-pyrones

✍ Scribed by Fabio Bellina; Matteo Biagetti; Adriano Carpita; Renzo Rossi

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
76 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

6-Alkyl-and 6-(1-alkenyl)-5-iodo-2-pyrones, which are available as major products by reaction of the corresponding (Z)-2-en-4-ynoic acids with iodine and NaHCO 3 in CH 3 CN, undergo insertion of activated zinc metal into their carbon iodine bond to provide the corresponding 5-(iodozinc)-2-pyrones. Hydrolysis of these organometallics gives 6-substituted 2-pyrones in satisfactory yields including two natural products. On the other hand, the Pd-catalyzed reaction of the organozincs either with an activated alkenyl halide or with activated and deactivated (hetero)aryl halides provides 5,6-disubstituted 2-pyrones in fair to good yields.

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