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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

✍ Scribed by Jurij Svete; Andrej Prešeren; Branko Stanovnik; Ljubo Golič; Simona Golič-Grdadolnik

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
420 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

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 azomethinimines 6a‐f to various dipolarophiles, which were found to proceed regio‐ and stereo‐selectively, afforded the corresponding pyrazolo[1,2‐a]‐pyrazoles 8a‐f, 10, and 13–16. Reaction of azomethinimine 6a with hydrogen cyanide gave rel‐(5__R__,6__R__)‐6‐benzoylamino‐5,6‐dihydro‐3,5‐diphenyl‐1‐oxo‐1__H__,7__H__‐pyrazolo[1,2‐a][1,2,3]triazole (18) as a representative of a new ring system.

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## 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

Reductive ring cleavage of 1-alkyl-4-ben
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
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## 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_