Syntheses of Spiro(2-oxopyrrolidinyl)-5,4 '-pyrazolones via Organocatalyzed Michael/Ammonolysis Cascade Reaction of 4-Aminopyrazolones and alpha,beta-Unsaturated Acyl Phosphates

The efficient organocatalyzed Michael/ammonolysis cascade reaction of N-protected 4-aminopyrazolones and alpha,beta-unsaturated acyl phosphates has been developed. This tactic gives rise to architecturally multifarious spiro(2-oxopyrrolidinyl)-5,4'-pyrazolones in good productiveness (up to 88%...

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Bibliographic Details
Published inSynlett Vol. 32; no. 9; pp. 923 - 929
Main Authors Li, You-Fen, Chen, Zheng-Jun, Jiao, Wen-Ya, Chen, Zhi-Jiao, Chen, Lin
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.06.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESIGN
pharmacophores
ASYMMETRIC-SYNTHESIS
Michael/ammonolysis cascade reaction
PYRAZOLONE DERIVATIVES
DISCOVERY
organocatalysis
POTENT
SPIROPYRAZOLONES
drug discovery
spiro(2-oxopyrrolidinyl)-5,4 '-pyrazolones
alpha,beta-unsaturated acyl phosphates
CONSTRUCTION
MOLECULAR-ORBITAL THEORY
N-protected 4-aminopyrazolones
medicinal chemistry
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Summary:The efficient organocatalyzed Michael/ammonolysis cascade reaction of N-protected 4-aminopyrazolones and alpha,beta-unsaturated acyl phosphates has been developed. This tactic gives rise to architecturally multifarious spiro(2-oxopyrrolidinyl)-5,4'-pyrazolones in good productiveness (up to 88% yield) and with moderate to good diastereoselectivities (up to 20:1 dr). These novel hybrid heterocycles would be promising candidates for drug-discovery programs and chemical biology.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1362-0296