Synthesis and conformational analysis of some spiropyrazoline isomers

Gábor Tóth, A. Lévai, A. Szöllösy, Helmut Duddeck

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

A series of spiropyrazolines has been synthesized by 1,3-dipolar cycloaddition of E- and Z-3-arylidene-chromanones, -1-thiochromanones, -flavanones, -1-thioflavanones as well as 2-benzylidene-1-indanone, -1-benzosuberone with diazomethane. It has been found that this cycloaddition is regio- and stereoselective affording trans- and cis- spiro-1-pyrazolines. Spiro-1-pyrazolines were converted into spiro-2-pyrazolines on acid-catalysed isomerization. Conformation and relative configuration of compounds prepared has been elucidated by various one- and two-dimensional n.m.r. methods.

Original languageEnglish
Pages (from-to)863-880
Number of pages18
JournalTetrahedron
Volume49
Issue number4
DOIs
Publication statusPublished - Jan 22 1993

Fingerprint

Cycloaddition
Cycloaddition Reaction
Isomers
Flavanones
Diazomethane
Isomerization
Conformations
Acids
thioflavanone
benzosuberone
indacrinone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and conformational analysis of some spiropyrazoline isomers. / Tóth, Gábor; Lévai, A.; Szöllösy, A.; Duddeck, Helmut.

In: Tetrahedron, Vol. 49, No. 4, 22.01.1993, p. 863-880.

Research output: Contribution to journalArticle

Tóth, Gábor ; Lévai, A. ; Szöllösy, A. ; Duddeck, Helmut. / Synthesis and conformational analysis of some spiropyrazoline isomers. In: Tetrahedron. 1993 ; Vol. 49, No. 4. pp. 863-880.
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