A new synthesis of 5-arylbenzo[c]xanthones from photoinduced electrocyclisation and oxidation of (E)-3-styrylflavones

Djenisa H A Rocha, Diana C G A Pinto, Artur M S Silva, T. Patonay, José A S Cavaleiro

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A new synthetic route to 5-arylbenzo[c]xanthones is -established. This was accomplished by use the Heck reaction of 3-bromoflavones with styrene derivatives, leading to (E)-3-styrylflavones with total diastereoselectivity. This transformation was greatly improved under microwave irradiation. The one-pot, photoinduced electrocyclisation of (E)-3-styrylflavones and further in situ oxidation of the cycloadduct leads to 5-arylbenzo[c]xan-thones.

Original languageEnglish
Pages (from-to)559-564
Number of pages6
JournalSynlett
Issue number4
DOIs
Publication statusPublished - 2012

Fingerprint

Xanthones
Styrene
Microwave irradiation
Derivatives
Oxidation

Keywords

  • Heck reaction
  • microwave irradiation
  • oxidation
  • photocyclisation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A new synthesis of 5-arylbenzo[c]xanthones from photoinduced electrocyclisation and oxidation of (E)-3-styrylflavones. / Rocha, Djenisa H A; Pinto, Diana C G A; Silva, Artur M S; Patonay, T.; Cavaleiro, José A S.

In: Synlett, No. 4, 2012, p. 559-564.

Research output: Contribution to journalArticle

Rocha, Djenisa H A ; Pinto, Diana C G A ; Silva, Artur M S ; Patonay, T. ; Cavaleiro, José A S. / A new synthesis of 5-arylbenzo[c]xanthones from photoinduced electrocyclisation and oxidation of (E)-3-styrylflavones. In: Synlett. 2012 ; No. 4. pp. 559-564.
@article{2f3992c6d1574524915d43630ba30d1a,
title = "A new synthesis of 5-arylbenzo[c]xanthones from photoinduced electrocyclisation and oxidation of (E)-3-styrylflavones",
abstract = "A new synthetic route to 5-arylbenzo[c]xanthones is -established. This was accomplished by use the Heck reaction of 3-bromoflavones with styrene derivatives, leading to (E)-3-styrylflavones with total diastereoselectivity. This transformation was greatly improved under microwave irradiation. The one-pot, photoinduced electrocyclisation of (E)-3-styrylflavones and further in situ oxidation of the cycloadduct leads to 5-arylbenzo[c]xan-thones.",
keywords = "Heck reaction, microwave irradiation, oxidation, photocyclisation",
author = "Rocha, {Djenisa H A} and Pinto, {Diana C G A} and Silva, {Artur M S} and T. Patonay and Cavaleiro, {Jos{\'e} A S}",
year = "2012",
doi = "10.1055/s-0031-1290355",
language = "English",
pages = "559--564",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "4",

}

TY - JOUR

T1 - A new synthesis of 5-arylbenzo[c]xanthones from photoinduced electrocyclisation and oxidation of (E)-3-styrylflavones

AU - Rocha, Djenisa H A

AU - Pinto, Diana C G A

AU - Silva, Artur M S

AU - Patonay, T.

AU - Cavaleiro, José A S

PY - 2012

Y1 - 2012

N2 - A new synthetic route to 5-arylbenzo[c]xanthones is -established. This was accomplished by use the Heck reaction of 3-bromoflavones with styrene derivatives, leading to (E)-3-styrylflavones with total diastereoselectivity. This transformation was greatly improved under microwave irradiation. The one-pot, photoinduced electrocyclisation of (E)-3-styrylflavones and further in situ oxidation of the cycloadduct leads to 5-arylbenzo[c]xan-thones.

AB - A new synthetic route to 5-arylbenzo[c]xanthones is -established. This was accomplished by use the Heck reaction of 3-bromoflavones with styrene derivatives, leading to (E)-3-styrylflavones with total diastereoselectivity. This transformation was greatly improved under microwave irradiation. The one-pot, photoinduced electrocyclisation of (E)-3-styrylflavones and further in situ oxidation of the cycloadduct leads to 5-arylbenzo[c]xan-thones.

KW - Heck reaction

KW - microwave irradiation

KW - oxidation

KW - photocyclisation

UR - http://www.scopus.com/inward/record.url?scp=84857459207&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84857459207&partnerID=8YFLogxK

U2 - 10.1055/s-0031-1290355

DO - 10.1055/s-0031-1290355

M3 - Article

SP - 559

EP - 564

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 4

ER -