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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-(4R,5R)-4-benzoylamino-5-phenyl-3-pyrazolidinone

✍ Scribed by Silvo Zupančič; Jurij Svete; Branko Stanovnik

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
241 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

The synthesis of pyrazolo[1,2-a]pyrazole
The synthesis of pyrazolo[1,2-a]pyrazoles. Regio- and stereo-selective 1,3-dipolar cycloadditions of (1Z)-rel-(4R,5R)-1-arylmethylene-4-benzoylamino-5-phenyl-3-pyrazolidinon-1 -azomethinimines
✍ Jurij Svete; Andrej Prešeren; Branko Stanovnik; Ljubo Golič; Simona Golič-Grdado 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 420 KB

## Abstract Reaction of __rel__‐(4__R__,5__R__)‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidinone (4) with aromatic aldehydes 5a‐f gave the corresponding (1__Z__)‐__rel__‐(4__R__,5__R__)‐1‐arylmethylene‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidinon‐1‐azomethinimines 6a‐f. 1,3‐Dipolar cycloadditions of azomethinim

Oxidative ring-opening of rel-(2R,3R,5S)
Oxidative ring-opening of rel-(2R,3R,5S)-5-aryl-2-benzoylamino-6,7-bis(methoxycarbonyl)-2,3-dihydro-1-oxo-3-phenyl-1H,5H-pyrazolo[1,2-a]-pyrazoles. Synthesis of rel-(2R,3R)-3-phenyl-3-[5-aryl-3,4-bis(methoxycarbonyl)pyrazolyl-1]alanine esters
✍ Andrej Prešeren; Jurij Svete; Branko Stanovnik 📂 Article 📅 1999 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 157 KB

## Abstract __rel__‐(2__R__,3__R__)‐__N__‐Benzoylamino‐6,7‐bis(methoxycarbonyl)‐2,3‐dihydro‐1‐oxo‐1__H__,5__H__‐pyrazolot[1,2‐__a__]‐pyrazoles 5, accesible by cycloaddition of dimethyl acetylenedicarboxylate (3) to (1Z)‐__rel__‐(4__R__,5__R__)‐1‐aryl‐methylidene‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidi