Dialkylation of Ethyl 4-(Het)aryl-3-oxobutanoates as a Route to 5-(2-Oxoethyl)cyclopentenones

Dialkylation of Ethyl 4-(Het)aryl-3-oxobutanoates as a Route to 5-(2-Oxoethyl)cyclopentenones Full article

Journal

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Output data

Year: 2019, Volume: 30, Number: 11, Pages: 1321-1323 Pages count : 3 DOI: 10.1055/s-0039-1689926

Authors

Lvov Andrey G. ¹ , Zakharov Alexey V. ¹ , Lyssenko Konstantin A. ² , Kachala Vadim V. ¹ , Shirinian Valerii Z. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
2	Department of Chemistry, Lomonosov Moscow State University, 119992 Moscow, Russian Federation

An unexplored ability of the long-known chemical transformation, Borsche’s cyclopentenone synthesis (the construction of a 1,4-diketone with subsequent base-induced cyclization), is reported. Double alkylation of ethyl 4-(het)aryl-3-oxobutanoates with 2-bromo-1-(het)arylethanones, with subsequent alkali treatment, provides access to cyclopentenones substituted with a 2-oxoethyl group at the 5-position. These products might serve as valuable synthons for heterocyclization, and this feature was demonstrated by synthesis of 4H-cyclopenta[b]thiophene derivatives.

Lvov A.G. , Zakharov A.V. , Lyssenko K.A. , Kachala V.V. , Shirinian V.Z.
Dialkylation of Ethyl 4-(Het)aryl-3-oxobutanoates as a Route to 5-(2-Oxoethyl)cyclopentenones
Synlett. 2019. V.30. N11. P.1321-1323. DOI: 10.1055/s-0039-1689926 WOS Scopus OpenAlex

Web of science:	WOS:000474772500009
Scopus:	2-s2.0-85067251462
OpenAlex:	W2946200649

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