Synthesis, characterization, and crystal structure of 2′,2″-dihydroxy-3,3⌄-bichalcone and its related chalcone-flavanone and biflavanone analogs

Carlos A. Escobar; Williams A. Fernández; Alexander Trujillo; Juan C. Santos; Thierry Roisnel; Mauricio Fuentealba

doi:10.1016/j.tetlet.2014.07.111

Synthesis, characterization, and crystal structure of 2′,2″-dihydroxy-3,3⌄-bichalcone and its related chalcone-flavanone and biflavanone analogs

Carlos A. Escobar, Williams A. Fernández, Alexander Trujillo, Juan C. Santos, Thierry Roisnel, Mauricio Fuentealba

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

The synthesis of 3,3′-diformyl-1,1′-biphenyl 1 and its reaction in basic media with 2′-hydroxyacetophenone and paeonol, respectively, are described. The products, a bichalcone 2, it's partially cyclized analog, a flavanone-chalcone 3 and the fully cyclized biflavanone 4, are reported as products for the first reaction, while only the chalcone 5 for the second. The crystalline and molecular structure, solved by X-ray diffraction analysis, for compounds 2 and 5 are also presented in this work.

Original language	English
Pages (from-to)	5271-5274
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2014.07.111
State	Published - 17 Sep 2014
Externally published	Yes

Keywords

Bichalcone
Biflavanone
Biphenyl
Chalcone
Flavanone-chalcone

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10.1016/j.tetlet.2014.07.111

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title = "Synthesis, characterization, and crystal structure of 2′,2″-dihydroxy-3,3⌄-bichalcone and its related chalcone-flavanone and biflavanone analogs",

abstract = "The synthesis of 3,3′-diformyl-1,1′-biphenyl 1 and its reaction in basic media with 2′-hydroxyacetophenone and paeonol, respectively, are described. The products, a bichalcone 2, it's partially cyclized analog, a flavanone-chalcone 3 and the fully cyclized biflavanone 4, are reported as products for the first reaction, while only the chalcone 5 for the second. The crystalline and molecular structure, solved by X-ray diffraction analysis, for compounds 2 and 5 are also presented in this work.",

keywords = "Bichalcone, Biflavanone, Biphenyl, Chalcone, Flavanone-chalcone",

author = "Escobar, {Carlos A.} and Fern{\'a}ndez, {Williams A.} and Alexander Trujillo and Santos, {Juan C.} and Thierry Roisnel and Mauricio Fuentealba",

note = "Funding Information: The authors gratefully acknowledge generous financial support from the FONDECYT – Chile Grants N° 1080147 and 1120785 , UNAB DI-57-12/R and PAI (Inserci{\'o}n de Capital Humano Avanzado) 791220008. The authors also acknowledge the LIA-MIF 836. Carlos A. Escobar thanks Dr. Dieter Sicker (Uni. Leipzig, Germany) for constant support, and Dr. Luis Espinoza Catal{\'a}n (Universidad T{\'e}cnica Federico Santa Maria, Valparaiso, Chile), for the NOESY experiments. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2014",

month = sep,

day = "17",

doi = "10.1016/j.tetlet.2014.07.111",

language = "English",

volume = "55",

pages = "5271--5274",

journal = "Tetrahedron Letters",

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T1 - Synthesis, characterization, and crystal structure of 2′,2″-dihydroxy-3,3⌄-bichalcone and its related chalcone-flavanone and biflavanone analogs

AU - Escobar, Carlos A.

AU - Fernández, Williams A.

AU - Trujillo, Alexander

AU - Santos, Juan C.

AU - Roisnel, Thierry

AU - Fuentealba, Mauricio

N1 - Funding Information: The authors gratefully acknowledge generous financial support from the FONDECYT – Chile Grants N° 1080147 and 1120785 , UNAB DI-57-12/R and PAI (Inserción de Capital Humano Avanzado) 791220008. The authors also acknowledge the LIA-MIF 836. Carlos A. Escobar thanks Dr. Dieter Sicker (Uni. Leipzig, Germany) for constant support, and Dr. Luis Espinoza Catalán (Universidad Técnica Federico Santa Maria, Valparaiso, Chile), for the NOESY experiments. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/9/17

Y1 - 2014/9/17

N2 - The synthesis of 3,3′-diformyl-1,1′-biphenyl 1 and its reaction in basic media with 2′-hydroxyacetophenone and paeonol, respectively, are described. The products, a bichalcone 2, it's partially cyclized analog, a flavanone-chalcone 3 and the fully cyclized biflavanone 4, are reported as products for the first reaction, while only the chalcone 5 for the second. The crystalline and molecular structure, solved by X-ray diffraction analysis, for compounds 2 and 5 are also presented in this work.

AB - The synthesis of 3,3′-diformyl-1,1′-biphenyl 1 and its reaction in basic media with 2′-hydroxyacetophenone and paeonol, respectively, are described. The products, a bichalcone 2, it's partially cyclized analog, a flavanone-chalcone 3 and the fully cyclized biflavanone 4, are reported as products for the first reaction, while only the chalcone 5 for the second. The crystalline and molecular structure, solved by X-ray diffraction analysis, for compounds 2 and 5 are also presented in this work.

KW - Bichalcone

KW - Biflavanone

KW - Biphenyl

KW - Chalcone

KW - Flavanone-chalcone

UR - http://www.scopus.com/inward/record.url?scp=84906957600&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.07.111

DO - 10.1016/j.tetlet.2014.07.111

M3 - Article

AN - SCOPUS:84906957600

VL - 55

SP - 5271

EP - 5274

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 38

ER -

Synthesis, characterization, and crystal structure of 2′,2″-dihydroxy-3,3⌄-bichalcone and its related chalcone-flavanone and biflavanone analogs

Abstract

Keywords

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