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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 ‐(4 R ,5 R )‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidinone
Author(s) -
Zupančič Silvo,
Svete Jurij,
Stanovnik Branko
Publication year - 1999
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.5570360305
Subject(s) - chemistry , sodium borohydride , raney nickel , alkyl , medicinal chemistry , ring (chemistry) , alkylation , potassium hydroxide , cleavage (geology) , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
rel ‐(4 R ,5 R )‐4‐Benzoylamino‐5‐phenyl‐3‐pyrazolidinone ( 1 ) was alkylated at position 1 with carbonyl compounds 2a‐g . The corresponding rel ‐(4 R ,5 R )‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidinone‐1‐azomethine imines 3a‐g , were treated with sodium borohydride to give rel ‐(4 R ,5 R )‐1‐alkyl‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidinones 4a‐g . Reduction of pyrazolidinones 4a‐g with Raney‐nickel alloy in methanolic potassium hydroxide furnished rel ‐(4 R ,5 R )‐ N ‐benzoyl‐3‐alkylamino‐3‐phenylalanine amides 5a‐f .