Diels-alder reactions with ethyl 1-benzofuran-3-carboxylates

Diels-alder reactions with ethyl 1-benzofuran-3-carboxylates Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2013, Volume: 49, Number: 6, Pages: 872-885 Pages count : 14 DOI: 10.1134/S1070428013060134

Authors

Kil'met'ev A.S. ¹ , Shul'ts E.E. ¹ , Shakirov M.M. ¹ , Rybalova T.V. ¹ , Tolstikov G.A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

Substituted salicylaldehydes reacted with ethyl diazoacetate to give ethyl 1-benzofuran-3-carboxylates containing various substituents in the aromatic ring. The Diels-Alder reaction of these compounds with Danishefsky's diene was regioselective, and it provided an effective method for the construction of the heterocyclic skeleton of hexahydrodibenzo[b,d]furan-7-one or tetrahydrodibenzo[b,d]furan-7-one. The adducts were found to undergo rearrangement to substituted 4'-hydroxybiphenyl-2-yl methyl carbonates during column chromatography on silica gel.

Kil'met'ev A.S. , Shul'ts E.E. , Shakirov M.M. , Rybalova T.V. , Tolstikov G.A.
Diels-alder reactions with ethyl 1-benzofuran-3-carboxylates
Russian Journal of Organic Chemistry. 2013. V.49. N6. P.872-885. DOI: 10.1134/S1070428013060134 WOS Scopus РИНЦ

Кильметьев А.С. , Шульц Э.Э. , Шакиров М.М. , Рыбалова Т.В. , Толстиков Г.А.
Диеновый синтез с участием этиловых эфиров бензо [b]фуран-3-карбоновых кислот
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №6. С.888-900. РИНЦ

Published print:	Jun 1, 2013
Published online:	Jul 6, 2013

Web of science	WOS:000321522400013
Scopus	2-s2.0-84880016260
Elibrary	20442438
OpenAlex	W2022518298