Synthesis of indazole-N-oxides via the 1,7-electrocyclisation of azomethine ylides

Miklós Nyerges, Imre Fejes, A. Virányi, Paul W. Groundwater, L. Tőke

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The first example of the 1,7-electrocyclisation of a non-stabilised azomethine ylide, e.g. 2, onto a nitro group, to give a 1,2,6-oxadiazepine intermediate, e.g. 4, is reported. Subsequent ring contraction results in the formation of the indazole-N-oxides 5, 12, and 14.

Original languageEnglish
Pages (from-to)5081-5083
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number30
DOIs
Publication statusPublished - Jul 23 2001

Fingerprint

Indazoles
Oxides
azomethine

Keywords

  • Cycloadditions
  • Electrocyclic reactions
  • Indazoles
  • Isoquinolines
  • Nitro compounds

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of indazole-N-oxides via the 1,7-electrocyclisation of azomethine ylides. / Nyerges, Miklós; Fejes, Imre; Virányi, A.; Groundwater, Paul W.; Tőke, L.

In: Tetrahedron Letters, Vol. 42, No. 30, 23.07.2001, p. 5081-5083.

Research output: Contribution to journalArticle

Nyerges, Miklós ; Fejes, Imre ; Virányi, A. ; Groundwater, Paul W. ; Tőke, L. / Synthesis of indazole-N-oxides via the 1,7-electrocyclisation of azomethine ylides. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 30. pp. 5081-5083.
@article{bf2cb39c2cc94c5e985b62d1a05488db,
title = "Synthesis of indazole-N-oxides via the 1,7-electrocyclisation of azomethine ylides",
abstract = "The first example of the 1,7-electrocyclisation of a non-stabilised azomethine ylide, e.g. 2, onto a nitro group, to give a 1,2,6-oxadiazepine intermediate, e.g. 4, is reported. Subsequent ring contraction results in the formation of the indazole-N-oxides 5, 12, and 14.",
keywords = "Cycloadditions, Electrocyclic reactions, Indazoles, Isoquinolines, Nitro compounds",
author = "Mikl{\'o}s Nyerges and Imre Fejes and A. Vir{\'a}nyi and Groundwater, {Paul W.} and L. Tőke",
year = "2001",
month = "7",
day = "23",
doi = "10.1016/S0040-4039(01)00892-9",
language = "English",
volume = "42",
pages = "5081--5083",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "30",

}

TY - JOUR

T1 - Synthesis of indazole-N-oxides via the 1,7-electrocyclisation of azomethine ylides

AU - Nyerges, Miklós

AU - Fejes, Imre

AU - Virányi, A.

AU - Groundwater, Paul W.

AU - Tőke, L.

PY - 2001/7/23

Y1 - 2001/7/23

N2 - The first example of the 1,7-electrocyclisation of a non-stabilised azomethine ylide, e.g. 2, onto a nitro group, to give a 1,2,6-oxadiazepine intermediate, e.g. 4, is reported. Subsequent ring contraction results in the formation of the indazole-N-oxides 5, 12, and 14.

AB - The first example of the 1,7-electrocyclisation of a non-stabilised azomethine ylide, e.g. 2, onto a nitro group, to give a 1,2,6-oxadiazepine intermediate, e.g. 4, is reported. Subsequent ring contraction results in the formation of the indazole-N-oxides 5, 12, and 14.

KW - Cycloadditions

KW - Electrocyclic reactions

KW - Indazoles

KW - Isoquinolines

KW - Nitro compounds

UR - http://www.scopus.com/inward/record.url?scp=0035939467&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035939467&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)00892-9

DO - 10.1016/S0040-4039(01)00892-9

M3 - Article

AN - SCOPUS:0035939467

VL - 42

SP - 5081

EP - 5083

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 30

ER -