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Reactions of 1,2‐dialkyl‐3‐pyrazolidinones
Author(s) -
Kornet Milton J.,
le Tan Sip
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060310
Subject(s) - chemistry , alkylation , reagent , alkyl , sodium hydride , yield (engineering) , aryl , medicinal chemistry , bromide , condensation , organic chemistry , benzyl bromide , hydride , allyl bromide , grignard reagent , catalysis , hydrogen , materials science , physics , metallurgy , thermodynamics
The condensation of 1,2‐dialkyl‐3‐pyrazoIidinones (1) with a series of aldehydes, ketones and esters in the presence of sodium hydride is described. Alkylation of I with several alkyl bromides gave 4‐alkyl substitution products in modest yield and reaction of 1,2,4‐trimethyl‐3‐pyrazolidinone with n‐butyl bromide gave a 4,4‐dialkylation product. Compound 1 reacted with aryl Grignard reagents to form 3‐aryl‐3‐pyrazoIines whereas the corresponding products were not realized in the case of alkyl Grignards. The reduction of a single example of 1 as well as the reduction of two 3‐pyrazolines to pyrazolidines is also reported.