1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis

László Tóth; Attila Kiss-Szikszai; Gábor Vasvári; Ferenc Fenyvesi; M. Vecsernyés; P. Mátyus; S. Antus; Attila Mándi; T. Kurtán

doi:10.1055/s-0037-1612085

1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis

László Tóth, Attila Kiss-Szikszai, Gábor Vasvári, Ferenc Fenyvesi, M. Vecsernyés, P. Mátyus, S. Antus, Attila Mándi, T. Kurtán

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Abstract

Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.

Original language	English
Pages (from-to)	799-803
Number of pages	5
Journal	Synlett
Volume	30
Issue number	7
DOIs	https://doi.org/10.1055/s-0037-1612085
Publication status	Published - Jan 1 2019

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Keywords

1,2-dihydrochromeno[2,3-c]pyrrol-3-one
antiproliferative
HPLC-ECD
isomerization
TDDFT-ECD

ASJC Scopus subject areas

Organic Chemistry

Cite this

Tóth, L., Kiss-Szikszai, A., Vasvári, G., Fenyvesi, F., Vecsernyés, M., Mátyus, P., Antus, S., Mándi, A., & Kurtán, T. (2019). 1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis. Synlett, 30(7), 799-803. https://doi.org/10.1055/s-0037-1612085

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abstract = "Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.",

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AU - Tóth, László

AU - Kiss-Szikszai, Attila

AU - Vasvári, Gábor

AU - Fenyvesi, Ferenc

AU - Vecsernyés, M.

AU - Mátyus, P.

AU - Antus, S.

AU - Mándi, Attila

AU - Kurtán, T.

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AB - Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.

KW - 1,2-dihydrochromeno[2,3-c]pyrrol-3-one

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KW - isomerization

KW - TDDFT-ECD

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Access to Document

10.1055/s-0037-1612085