Novel approach for the synthesis of 2-arylfuro[3,2-b]pyran-3-carbaldehydes based on acid-catalyzed cyclization of allomaltol containing enaminones

Novel approach for the synthesis of 2-arylfuro[3,2-b]pyran-3-carbaldehydes based on acid-catalyzed cyclization of allomaltol containing enaminones Full article

Journal

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

Output data

Year: 2023, Volume: 53, Number: 1, Pages: 58-67 Pages count : 10 DOI: 10.1080/00397911.2022.2150975

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, Russia

The novel and efficient approach for the synthesis of various 2-arylsubstituted furo[3,2-b]pyran-3-carbaldehydes was developed. The studied method is based on acid-catalyzed cyclization of enaminones bearing allomaltol fragment. The distinctive feature of the suggested protocol is the other direction of heterocyclization of starting enaminoketones in contrast to the previously described approach leading to 3-aroylfuro[3,2-b]pyranes. The advantages of this synthesis are easily accessible starting compounds, mild reaction conditions, and simple workup procedure avoiding chromatographic purification. The synthetic utility of obtained aldehydes was demonstrated by the preparation of various derivatives. The structure of one furo[3,2-b]pyran-3-carbaldehyde was proved by X-ray diffraction.

Komogortsev A.N. , Lichitsky B.V. , Melekhina V.G.
Novel approach for the synthesis of 2-arylfuro[3,2-b]pyran-3-carbaldehydes based on acid-catalyzed cyclization of allomaltol containing enaminones
Synthetic Communications. 2023. V.53. N1. P.58-67. DOI: 10.1080/00397911.2022.2150975 WOS Scopus OpenAlex

Web of science:	WOS:000914249900006
Scopus:	2-s2.0-85142853222
OpenAlex:	W4310009669

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