Ring‐Expansion of Cyclopropyl Ketones to Furans

In this paper, a fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogues can be obtained from commercial sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Ring‐Expansion of Cyclopropyl Ketones to Furans

Abstract: Abstract. Rigid cyclopropyl ketones were rearranged by phosphorus pentachloride to furans. This ring-expansion was also possible using bromine and an acid. A f3, y-unsaturated ketone, a supposed intermediate in the reaction, gave furan products when treated with bromine alone.

Cited by 2 publications

References 8 publications

ChemInform Abstract: RING‐EXPANSION OF CYCLOPROPYL KETONES TO FURANS

ChemInform Abstract: RING‐EXPANSION OF CYCLOPROPYL KETONES TO FURANS

Regioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones

Contact Info

Product

Resources

About