Synthesis of furo[2,3-f]isoquinolines by aromatic Claisen rearrangement and subsequent cyclization

Mercedes Törincsi, P. Kolonits, Endre Pálosi, L. Novák

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Furo[2,3-f]isoquinolines were prepared by reacting isoquinolin-5-ol with an allyl bromide. Reaction between the sodium salt of isoquinolinol and and allyl bromide led to the formation of an allyloxyisoquinoline, which was thermally rearranged. The resultant allylisoquinoline was then subjected to acid-catalyzed cyclization to afford the title compound.

Original languageEnglish
Pages (from-to)284-288
Number of pages5
JournalSynthesis
Issue number2
DOIs
Publication statusPublished - Jan 17 2007

Fingerprint

Isoquinolines
Cyclization
Sodium
Salts
Acids
allyl bromide

Keywords

  • Allyl aryl ethers
  • Claisen rearrangement
  • Furo[2,3-f]isoquinoline
  • Ring closure
  • Sonochemical conditions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of furo[2,3-f]isoquinolines by aromatic Claisen rearrangement and subsequent cyclization. / Törincsi, Mercedes; Kolonits, P.; Pálosi, Endre; Novák, L.

In: Synthesis, No. 2, 17.01.2007, p. 284-288.

Research output: Contribution to journalArticle

@article{40313d5dd30d4624aca929f77c742551,
title = "Synthesis of furo[2,3-f]isoquinolines by aromatic Claisen rearrangement and subsequent cyclization",
abstract = "Furo[2,3-f]isoquinolines were prepared by reacting isoquinolin-5-ol with an allyl bromide. Reaction between the sodium salt of isoquinolinol and and allyl bromide led to the formation of an allyloxyisoquinoline, which was thermally rearranged. The resultant allylisoquinoline was then subjected to acid-catalyzed cyclization to afford the title compound.",
keywords = "Allyl aryl ethers, Claisen rearrangement, Furo[2,3-f]isoquinoline, Ring closure, Sonochemical conditions",
author = "Mercedes T{\"o}rincsi and P. Kolonits and Endre P{\'a}losi and L. Nov{\'a}k",
year = "2007",
month = "1",
day = "17",
doi = "10.1055/s-2006-958954",
language = "English",
pages = "284--288",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "2",

}

TY - JOUR

T1 - Synthesis of furo[2,3-f]isoquinolines by aromatic Claisen rearrangement and subsequent cyclization

AU - Törincsi, Mercedes

AU - Kolonits, P.

AU - Pálosi, Endre

AU - Novák, L.

PY - 2007/1/17

Y1 - 2007/1/17

N2 - Furo[2,3-f]isoquinolines were prepared by reacting isoquinolin-5-ol with an allyl bromide. Reaction between the sodium salt of isoquinolinol and and allyl bromide led to the formation of an allyloxyisoquinoline, which was thermally rearranged. The resultant allylisoquinoline was then subjected to acid-catalyzed cyclization to afford the title compound.

AB - Furo[2,3-f]isoquinolines were prepared by reacting isoquinolin-5-ol with an allyl bromide. Reaction between the sodium salt of isoquinolinol and and allyl bromide led to the formation of an allyloxyisoquinoline, which was thermally rearranged. The resultant allylisoquinoline was then subjected to acid-catalyzed cyclization to afford the title compound.

KW - Allyl aryl ethers

KW - Claisen rearrangement

KW - Furo[2,3-f]isoquinoline

KW - Ring closure

KW - Sonochemical conditions

UR - http://www.scopus.com/inward/record.url?scp=33947520361&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947520361&partnerID=8YFLogxK

U2 - 10.1055/s-2006-958954

DO - 10.1055/s-2006-958954

M3 - Article

SP - 284

EP - 288

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 2

ER -