Synthesis, characterization and crystal structure of 4′-ethynylflavanone and its chalcone precursor

Ismael Salinas-Ortega, Fernanda Ocayo, Juan C. Santos, Alexander Trujillo, Carlos A. Escobar

Resultado de la investigación: Article

Resumen

The synthesis of (E)-4-ethynyl-2′-hydroxychalcone (7) and the 4′-ethynylflavanone (8), it's spectroscopic and X-ray characterization are described for both compounds. Products were prepared by reacting 4-bromobenzaldehyde (1) under Sonogashira coupling reaction conditions, in order to obtain the key intermediary 4-ethynylbenzaldehyde (3). Then, this intermediary was reacted with 2′-hydroxyacetophenone (4) under Claisen-Shchmidt conditions to render a mixture of (E)-4-ethynyl-2′-hydroxychalcone (7) and 4′-ethynylflavanone (8). Compounds were separated by column chromatography, and spectroscopically characterized. Also, an alternative synthetic route to 4′-ethynylflavanone (8) was tested; the known 4′-bromoflavanone (6) was reacted under Sonogashira coupling conditions, in order to obtain the intermediary 4′-(trimethylsilylethynyl)-flavanone (9), which under deprotection afforded the desired 4′-ethynylflavanone (8). The Synthesis of (E)-4-bromo-2′-hydroxychalcone (5) and 4′-bromoflavanone (6), used as precursors, is also described. The X-ray structure of (E)-4-bromo-2′-hydroxychalcone (5) is presented as well.

Idioma originalEnglish
Páginas (desde-hasta)361-367
Número de páginas7
PublicaciónJournal of Molecular Structure
Volumen1128
DOI
EstadoPublished - 15 ene 2017

Huella dactilar

Chalcone
Crystal structure
X rays
Column chromatography
2'-hydroxychalcone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

Citar esto

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title = "Synthesis, characterization and crystal structure of 4′-ethynylflavanone and its chalcone precursor",
abstract = "The synthesis of (E)-4-ethynyl-2′-hydroxychalcone (7) and the 4′-ethynylflavanone (8), it's spectroscopic and X-ray characterization are described for both compounds. Products were prepared by reacting 4-bromobenzaldehyde (1) under Sonogashira coupling reaction conditions, in order to obtain the key intermediary 4-ethynylbenzaldehyde (3). Then, this intermediary was reacted with 2′-hydroxyacetophenone (4) under Claisen-Shchmidt conditions to render a mixture of (E)-4-ethynyl-2′-hydroxychalcone (7) and 4′-ethynylflavanone (8). Compounds were separated by column chromatography, and spectroscopically characterized. Also, an alternative synthetic route to 4′-ethynylflavanone (8) was tested; the known 4′-bromoflavanone (6) was reacted under Sonogashira coupling conditions, in order to obtain the intermediary 4′-(trimethylsilylethynyl)-flavanone (9), which under deprotection afforded the desired 4′-ethynylflavanone (8). The Synthesis of (E)-4-bromo-2′-hydroxychalcone (5) and 4′-bromoflavanone (6), used as precursors, is also described. The X-ray structure of (E)-4-bromo-2′-hydroxychalcone (5) is presented as well.",
keywords = "2-(p-ethynylphenyl)-chroman-4-one, 2′-Hydroxychalcone, Chalcone, Ethynylchalcone, Ethynylflavanone, Flavanone",
author = "Ismael Salinas-Ortega and Fernanda Ocayo and Santos, {Juan C.} and Alexander Trujillo and Escobar, {Carlos A.}",
year = "2017",
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language = "English",
volume = "1128",
pages = "361--367",
journal = "Journal of Molecular Structure",
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TY - JOUR

T1 - Synthesis, characterization and crystal structure of 4′-ethynylflavanone and its chalcone precursor

AU - Salinas-Ortega, Ismael

AU - Ocayo, Fernanda

AU - Santos, Juan C.

AU - Trujillo, Alexander

AU - Escobar, Carlos A.

PY - 2017/1/15

Y1 - 2017/1/15

N2 - The synthesis of (E)-4-ethynyl-2′-hydroxychalcone (7) and the 4′-ethynylflavanone (8), it's spectroscopic and X-ray characterization are described for both compounds. Products were prepared by reacting 4-bromobenzaldehyde (1) under Sonogashira coupling reaction conditions, in order to obtain the key intermediary 4-ethynylbenzaldehyde (3). Then, this intermediary was reacted with 2′-hydroxyacetophenone (4) under Claisen-Shchmidt conditions to render a mixture of (E)-4-ethynyl-2′-hydroxychalcone (7) and 4′-ethynylflavanone (8). Compounds were separated by column chromatography, and spectroscopically characterized. Also, an alternative synthetic route to 4′-ethynylflavanone (8) was tested; the known 4′-bromoflavanone (6) was reacted under Sonogashira coupling conditions, in order to obtain the intermediary 4′-(trimethylsilylethynyl)-flavanone (9), which under deprotection afforded the desired 4′-ethynylflavanone (8). The Synthesis of (E)-4-bromo-2′-hydroxychalcone (5) and 4′-bromoflavanone (6), used as precursors, is also described. The X-ray structure of (E)-4-bromo-2′-hydroxychalcone (5) is presented as well.

AB - The synthesis of (E)-4-ethynyl-2′-hydroxychalcone (7) and the 4′-ethynylflavanone (8), it's spectroscopic and X-ray characterization are described for both compounds. Products were prepared by reacting 4-bromobenzaldehyde (1) under Sonogashira coupling reaction conditions, in order to obtain the key intermediary 4-ethynylbenzaldehyde (3). Then, this intermediary was reacted with 2′-hydroxyacetophenone (4) under Claisen-Shchmidt conditions to render a mixture of (E)-4-ethynyl-2′-hydroxychalcone (7) and 4′-ethynylflavanone (8). Compounds were separated by column chromatography, and spectroscopically characterized. Also, an alternative synthetic route to 4′-ethynylflavanone (8) was tested; the known 4′-bromoflavanone (6) was reacted under Sonogashira coupling conditions, in order to obtain the intermediary 4′-(trimethylsilylethynyl)-flavanone (9), which under deprotection afforded the desired 4′-ethynylflavanone (8). The Synthesis of (E)-4-bromo-2′-hydroxychalcone (5) and 4′-bromoflavanone (6), used as precursors, is also described. The X-ray structure of (E)-4-bromo-2′-hydroxychalcone (5) is presented as well.

KW - 2-(p-ethynylphenyl)-chroman-4-one

KW - 2′-Hydroxychalcone

KW - Chalcone

KW - Ethynylchalcone

KW - Ethynylflavanone

KW - Flavanone

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U2 - 10.1016/j.molstruc.2016.09.005

DO - 10.1016/j.molstruc.2016.09.005

M3 - Article

AN - SCOPUS:84986274577

VL - 1128

SP - 361

EP - 367

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

ER -