Reductive ring cleavage of 1-alkyl-4-benzoylamino-5-phenyl-3-pyrazolidinones with Raney-nickel alloy. Synthesis of N-benzoyl-3-alkylamino-3-phenylalanine amides from rel-(4R,5R)-4-benzoylamino-5-phenyl-3-pyrazolidinone

Authors
Zupancic, S Svete, J Stanovnik, B
Citation
S. Zupancic et al., Reductive ring cleavage of 1-alkyl-4-benzoylamino-5-phenyl-3-pyrazolidinones with Raney-nickel alloy. Synthesis of N-benzoyl-3-alkylamino-3-phenylalanine amides from rel-(4R,5R)-4-benzoylamino-5-phenyl-3-pyrazolidinone, J HETERO CH, 36(3), 1999, pp. 607-610
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
36
Issue
3
Year of publication
1999
Pages
607 - 610
Database
ISI
SICI code
0022-152X(199905/06)36:3<607:RRCO1>2.0.ZU;2-F
Abstract
rel-(4R,5R)-3-Benzoylamino-5-phenyl-3-pyrazolidinone (1) was alkylated at p osition 1 with carbonyl compounds 2a-g. The corresponding rel-(4R,5R)-4-ben zoylamino-5-phenyl-3-pyrazolidinone-1-azomethine imines 3a-g, were treated with sodium borohydride to give rel-(4R,SR)-1-alkyl-4-benzoylamino-5-phenyl -3-pyrazolidinones 4a-g. Reduction of pyrazolidinones 4a-g with Raney-nicke l alloy in methanolic potassium hydroxide furnished rel-(4R,SR)-N-benzoyl-3 -alkylamino-3-phenylalanine amides 5a-f.