Synthesis of Spiro[pyrrole-3,2'-pyrrolo[2,1-b]oxazoles] via 1,3-Dipolar Cycloaddition of 1H-Pyrrole-2,3-diones to Azomethine Ylides

The 1,3-dipolar cycloaddition of 1 H -pyrrole-2,3-diones to azomethine ylides generated in situ by the condensation of L-proline and arylcarbaldehydes proceeds regio- and diastereoselectively to form substituted ethyl 1,2,5',6',7',7a'-hexahydro-3' H -spiro[pyrrole-3,2'-...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-11, Vol.59 (11), p.1867-1873
Main Authors: Moroz, A. A., Dmitriev, M. V., Maslivets, A. N.
Format: Article
Language:English
Subjects:
Carboxylates
Chemistry
Chemistry and Materials Science
Cycloaddition
Organic Chemistry
Oxazole
Single crystals
X ray analysis
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Summary:The 1,3-dipolar cycloaddition of 1 H -pyrrole-2,3-diones to azomethine ylides generated in situ by the condensation of L-proline and arylcarbaldehydes proceeds regio- and diastereoselectively to form substituted ethyl 1,2,5',6',7',7a'-hexahydro-3' H -spiro[pyrrole-3,2'-pyrrolo[2,1- b ]oxazole]-4-carboxylates. The structure of the synthesized ethyl (3 R *,3' R *,7a' S *)-3'-(4-bromophenyl)-2-oxo-1,5-diphenyl-1,2,5',6',7',7a'-hexahydro-3' H -spiro[pyrrole-3,2'-pyrrolo[2,1- b ]oxazole]-4-carboxylate was confirmed by single crystal X-ray analysis.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023110040