Regioselective ring opening of aziridine for synthesizing azaheterocycle
Aziridine had different regioselective ring openings depending on the functional group of its alkyl substituent. In the case of the alkyl group bearing γ-ketone at the C2 substituent of aziridine, the ring opening by the hydroxy nucleophile from H 2 O occurred by attacking the aziridine carbon at th...
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| Published in: | Frontiers in chemistry Vol. 11; p. 1280633 |
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| Main Authors: | , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Frontiers Media S.A
19-10-2023
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| Subjects: | |
| Online Access: | Get full text |
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| Summary: | Aziridine had different regioselective ring openings depending on the functional group of its alkyl substituent. In the case of the alkyl group bearing γ-ketone at the C2 substituent of aziridine, the ring opening by the hydroxy nucleophile from H
2
O occurred by attacking the aziridine carbon at the C2 position. This reaction proceeded efficiently in the presence of CF
3
CO
2
H. Interestingly, the same starting aziridine ring bearing the alkyl substituent at the C2 position with the γ-silylated hydroxy group instead of γ-ketone led to the ring-opening reaction by the same oxygen nucleophile at the unsubstituted C3 position, with the breakage of the bond between aziridine N1 nitrogen and carbon at C3. These reaction products were cyclized to afford substituted pyrrolidine and piperidine rings with representative examples of congeners of pseudoconhydrine and monomorine. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Joel Teran, Instituto de Ciencias, Mexico Reviewed by: Turan Ozturk, Istanbul Technical University, Türkiye Edited by: Hasan Küçükbay, İnönü University, Türkiye |
| ISSN: | 2296-2646 2296-2646 |
| DOI: | 10.3389/fchem.2023.1280633 |