Generation and cycloaddition of polymer-supported azomethine imines: traceless synthesis of pyrazole derivatives from α-silylnitrosoamide derivatives bound to resin

1,3-Dipolar cycloaddition of polymer-supported azomethine imines with dimethyl acetylenedicarboxylate (DMAD) gave pyrazole derivatives in good yields. The azomethine imines were generated from polymer-supported α-silylnitrosoamides by a 1,4-silatropic shift. The feature of this reaction is that no c...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 5; pp. 691 - 695
Main Authors Washizuka, Ken-Ichi, Nagai, Keiko, Minakata, Satoshi, Ryu, Ilhyong, Komatsu, Mitsuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.01.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANGLE-SPINNING NMR
COMBINATORIAL ORGANIC-SYNTHESIS
TECHNOLOGIES
SOLID-PHASE SYNTHESIS
1,3-DIPOLAR CYCLOADDITION
DRUG DISCOVERY
LIBRARY
STEREOSELECTIVE SYNTHESIS
CYCLIZATION
HIGHLY FUNCTIONALIZED PYRROLIDINES
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Summary:1,3-Dipolar cycloaddition of polymer-supported azomethine imines with dimethyl acetylenedicarboxylate (DMAD) gave pyrazole derivatives in good yields. The azomethine imines were generated from polymer-supported α-silylnitrosoamides by a 1,4-silatropic shift. The feature of this reaction is that no cleavage operations are required after the cycloaddition.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)02140-1