Cyclocondensations of (+)-camphor derived enaminones with hydrazine derivatives

Reactions of 3-[( E)-(dimethylamino)methylidene]-(+)-camphor and (1 R,5 S)-4-[( E)-(dimethylamino)methylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one with hydrazine derivatives were studied. Treatment of 3-[( E)-(dimethylamino)methylidene]-(+)-camphor with hydrazines afforded the correspondi...

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Published inTetrahedron Vol. 61; no. 16; pp. 3991 - 3998
Main Authors Grošelj, Uroš, Bevk, David, Jakše, Renata, Rečnik, Simon, Meden, Anton, Stanovnik, Branko, Svete, Jurij
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.04.2005
Elsevier
Subjects
Camphor
Chemistry
Chemistry, Organic
Condensations
Enaminones
Hydrazines
Physical Sciences
Science & Technology
Terpenes
Condensations
Hydrazines
Enaminones
Terpenes
Camphor
hydrazines
terpenes
camphor
condensations
CHIRAL HETEROCYCLIC LIGANDS
enaminones
SOLUTION-PHASE SYNTHESIS
3-(DIMETHYLAMINO)PROPENOATES
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Summary:Reactions of 3-[( E)-(dimethylamino)methylidene]-(+)-camphor and (1 R,5 S)-4-[( E)-(dimethylamino)methylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one with hydrazine derivatives were studied. Treatment of 3-[( E)-(dimethylamino)methylidene]-(+)-camphor with hydrazines afforded the corresponding fused pyrazoles. Similarly, fused pyrazoles were obtained upon reaction of (1 R,5 S)-4-[( E)-(dimethylamino)methylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one with ortho-unsubstituted phenylhydrazines, while reactions with ortho-substituted phenylhydrazines and with hydrazine hydrochloride resulted in ‘ring switching’ type of transformation to furnish 2-aryl-4-[(1 S,3 R)-3-hydroxy-2,2,3-trimethylcyclopentyl]-1,2-dihydro-3 H-pyrazol-3-ones. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.02.048