Synthesis of substituted 2-arylfuro[3,2-b]pyrans via acid-catalyzed recyclization of 2-aminofurans containing allomaltol fragment

Abstract

For the first time, we elaborated a novel one-step approach for the synthesis of 2-arylfuro[3,2-b]pyran derivatives. The suggested method is based on acid-catalyzed recyclization of 2-aminofurans bearing allomaltol fragment. It was shown that starting 2-amino-3-cyanofurans are converted into the corresponding 2-arylfuro[3,2-b]pyrans containing a cyanomethyl fragment. At the same time, reaction of similar ester derivatives leads to carbamoyl analogues. The advantages of the studied method are the use of readily available starting compounds and simple work-up procedure which can avoid chromatographic purification. The structure of one of synthesized products was determined by X-Ray diffraction.

Graphical abstract

Keywords:

• Acid-catalyzed recyclization
• allomaltol
• 2-aminofurans
• 2-arylfuro[3,2-b]pyrans
• one-step approach

Acknowledgments

Crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic Chemistry, Moscow.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Data availability statement

Data available within the article or its supplementary materials.