Publication Date:
2014-05-15
Description:
The oxidative cyclization reactions of 1,3-dicarbonyl compounds 1a – 1c and α , β -unsaturated alcohols 2a – 2f with Mn(OAc) 3 were performed, leading to dihydrofurans. Treatment of 1a and 1b with 2-methylbut-3-en-2-ol ( 2a ) gave dihydrofurans 3aa and 3ba , and dihydropyrans 4aa and 4ba , as unexpected products. While the reaction of 2-methylbut-3-yn-2-ol ( 2b ) with acetylacetone ( 1b ) yielded a bifuran, ethyl acetoacetate ( 1a ) led to a mixture of furan, bifuran, and salicylate derivatives. Besides, surprisingly, styryl-substituted dihydrofurans were obtained from the reactions of 1,3-dicarbonyl compounds and (3 E )-2,4-diphenylbut-3-en-2-ol. The reaction mechanisms were proposed for the formation of the different products, considering intermediates in these reaction mixtures.
Print ISSN:
0018-019X
Electronic ISSN:
1522-2675
Topics:
Chemistry and Pharmacology
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