6533b82efe1ef96bd1293090

RESEARCH PRODUCT

Cycloaddition reactions of 1-tert-butyl-4-vinylpyrazole

Lourdes Piqueres-vidalJosé Sepúlveda-arquesMercedes Medio-simón

subject

Dimethyl acetylenedicarboxylateTert butylchemistry.chemical_compoundIndazolechemistryMethyl propiolateDiels alderSubstituentOrganic chemistryGeneral ChemistryTetracyanoethyleneMedicinal chemistryCycloaddition

description

1-tert-Butyl-4-vinylpyrazole1 a reacts with dimethyl acetylenedicarboxylate (DMAD), methyl propiolate (MP) and N-phenylmaleimide (NPMI) affording the indazole derivatives2,3, and5 as a result of a Diels-Alder ([4 + 2]) cycloaddition. With diethylazodicarboxylate (DEAZD), tetracyanoethylene (TCNE) and 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) the reaction takes place exclusively through the olefinic substituent and the adducts6,7, and9 were isolated. The alkenylpyrazoles1 b–d reacted withDMAD and N-phenylmaleimide to give polymers.

yearjournalcountryeditionlanguage
1989-12-01Monatshefte f�r Chemie Chemical Monthly
https://doi.org/10.1007/bf00809294