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1,3-Dipolar cycloadditions of (4R*,5R*)-1-alkylidene-4-(benzoylamino)-5-phenyl-3-pyrazolidinon-1-azomethine imines

✍ Scribed by Lidija Pezdirc; Uroš Grošelj; Anton Meden; Branko Stanovnik; Jurij Svete

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
667 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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1,3‐Dipolar cycloadditions of azomethine imines 3a and 3b, available by acid‐catalyzed treatment of 3‐pyrazolidinone 1 with acetone (2a) and butyraldehyde (2b), respectively, were studied. Reactions of 3a with DMAD (4) afforded a mixture of products 9 and 10a, whilst treatment of 3b with DMAD (4) gave a mixture of compound 9 and epimeric cycloadducts 10/10′b. On the other hand, cycloadducts 13a,b‐16a,b were isolated as single diastereomers in 9–37% yields upon reactions of 3a,b with olefinic dipolarophiles 5–8. The structures of cycloadducts 9, 10a, 10/10′b, and 13a,b‐16a,b were determined by ^1^H nmr and NOESY spectroscopy. The structure of compound 13a was confirmed by X‐ray diffraction.

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