Synthesis of 3-Amino-5-fluoroalkylfurans by Intramolecular Cyclization

Clotilde Plaçais, Morgan Donnard, Armen Panossian, Jean-Pierre Vors, David Bernier, Sergii Pazenok and Frédéric R. Leroux*

*Université de Strasbourg, Université de Haute-Alsace, CNRS, UMR 7042-LIMA, ECPM, 25 Rue Becquerel, Strasbourg 67087, France, Email: frederic.lerouxunistra.fr

C. Plaçais, M. Donnard, A. Panossian, J.-P. Vors, D. Bernier, S. Pazenok, F. R. Leroux, Org. Lett., 2021, 23, 4915-4919.

DOI: 10.1021/acs.orglett.1c01672

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Abstract

A rapid and convenient cyclization of easily accessible fluorovinamides provides 3-amino-5-fluoroalkylfuran hydrochloride salts in excellent yields. The reaction tolerates four different fluorinated groups (-CF₃, -CF₂CF₃, -CHF₂, and -CF₂Cl) and a wide range of substituents on the amine.

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proposed mechanism

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General procedure for the formation of furans

To the corresponding fluorinated starting material (0.4 mmol) in MeOH (2 mL) was slowly added SOCl₂ (1 eq., 0.4 mmol) at 0 °C, and the mixture was left to stir at room temperature for 0.5 hour. The reaction mixture was then concentrated to give the pure product as a hydrochloride. The obtained products did not require further purification.

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Key Words

furans

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ID: J54-Y2021