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http://hdl.handle.net/123456789/4466
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DC Field | Value | Language |
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dc.contributor.author | Mandal, Sanjay K. | - |
dc.date.accessioned | 2023-08-10T10:55:21Z | - |
dc.date.available | 2023-08-10T10:55:21Z | - |
dc.date.issued | 2022 | - |
dc.identifier.citation | ChemistrySelect, 7(37), 2202172 | en_US |
dc.identifier.uri | https://doi.org/10.1002/slct.202202172 | - |
dc.identifier.uri | http://hdl.handle.net/123456789/4466 | - |
dc.description | Only IISERM authors are available in the record | en_US |
dc.description.abstract | Herein, we describe synthesis of functionalized thiophenyl acetyl-hydrazones using acetyl-thiophene derivative as precursor which further underwent Vilsmeier-Haack reaction in an unexpected manner, providing three-carbon atoms to the molecular framework. The mechanistic view explained formation of C2-formamide(thiophene)pyrazolyl-C4’-carbaldehyde by three consecutive actions in single-pot: 1) nucleophilic amino to C2-iminium ion generation, 2) cyclization to pyrazole ring and 3) nucleophilic attack by pyrazole to C4’-iminium ion which finally leads to dual formylation in the system. This product burst to primary amines to synthesize highly substituted C2-formamide(thiophene)pyrazolyl-C4’-Schiff's bases. Further, the reactivity of synthesized Schiff's bases underwent metal-free ring closure with diverse heteroatomic ketene sources which exposed the emergence of stereoselective trans-β-lactams. The broad functional groups encircled monocyclic β-lactams were achieved in moderate to excellent yields under gentle conditions. Additionally, theoretical calculations on B3LYP/6-31G(d,p) level of some representative compounds are also investigated to support mechanistic explanation with their stabilized structures and physical properties. | en_US |
dc.language.iso | en_US | en_US |
dc.publisher | Chemistry Europe | en_US |
dc.subject | Schiff's Bases | en_US |
dc.subject | Vilsmeier-Haack reaction | en_US |
dc.title | Synthesis of C2-Formamide(thiophene)pyrazolyl-C4’-carbaldehyde and their Transformation to Schiff's Bases and Stereoselective trans-β-Lactams: Mechanistic and Theoretical Insights | en_US |
dc.type | Article | en_US |
Appears in Collections: | Research Articles |
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