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

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

Journal

Synthetic Communications
ISSN: 1532-2432 , E-ISSN: 0039-7911

Output data

Year: 2023, Volume: 53, Number: 10, Pages: 720-730 Pages count : 11 DOI: 10.1080/00397911.2023.2191856

Authors

Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Melekhina Valeriya G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Moscow, Russian Federation

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.

Komogortsev A.N. , Lichitsky B.V. , Melekhina V.G.
Synthesis of substituted 2-arylfuro[3,2-b]pyrans via acid-catalyzed recyclization of 2-aminofurans containing allomaltol fragment
Synthetic Communications. 2023. V.53. N10. P.720-730. DOI: 10.1080/00397911.2023.2191856 WOS Scopus OpenAlex

Web of science:	WOS:000956075100001
Scopus:	2-s2.0-85150938066
OpenAlex:	W4360852175

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