General and Versatile Entry to 4,5-Fused Polycyclic Imidazolones Systems. Use of the Tandem Transposition/π-Cyclization of N-Acyliminium Species.
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| Title: | General and Versatile Entry to 4,5-Fused Polycyclic Imidazolones Systems. Use of the Tandem Transposition/π-Cyclization of N-Acyliminium Species. |
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| Authors: | Anthony Pesquet1, Daïch, Adam1 adam.daich@univ-lehavre.fr, van Hijfte, Luc2 adam.daich@univ-lehavre.fr |
| Source: | Journal of Organic Chemistry. 7/7/2006, Vol. 71 Issue 14, p5303-5311. 9p. 1 Diagram. |
| Subjects: | Physical & theoretical chemistry, Imidazoles, Organic compounds, Ketones, Hydantoin |
| Abstract: | A simple and efficient methodology for the synthesis of 4,5-fused imidazolidin-2-ones from bicyclic and tricyclic ketones in a four-step sequence was described, by successive spirohydantoin Bucherer-Berg formation, mono- and dialkylation of the nitrogen atom of the hydantoin ring, regioselective reduction of one carbonyl function, and cationic cyclization associated with ring expansion. The key step of this sequential reaction was based on a tandem transposition/intramolecular amidoalkylation of cyclic spiro-N-acyliminium species. The process seems to be easy, general, regiospecific, resulted in the formation of polyheterocyclic systems containing an imidazolidin-2-one nucleus in good to excellent yields (67-99%), and is compatible with a large-scale production (up to 3 g of product 14, for example). Also, this method allows the preparation of the novel heterocycles 14 and 15 that have pharmaceutically interesting profiles, which are not accessible through short current synthetic methods. Finally, products 15 bear a secondary amide function crucial for further transformations, including the introduction of various pharmacophore groups either at the C or the N atoms of the imidazole ring. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 21809846 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: General and Versatile Entry to 4,5-Fused Polycyclic Imidazolones Systems. Use of the Tandem Transposition/π-Cyclization of N-Acyliminium Species. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Anthony+Pesquet%22">Anthony Pesquet</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Daïch%2C+Adam%22">Daïch, Adam</searchLink><relatesTo>1</relatesTo><i> adam.daich@univ-lehavre.fr</i><br /><searchLink fieldCode="AR" term="%22van+Hijfte%2C+Luc%22">van Hijfte, Luc</searchLink><relatesTo>2</relatesTo><i> adam.daich@univ-lehavre.fr</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 7/7/2006, Vol. 71 Issue 14, p5303-5311. 9p. 1 Diagram. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Physical+%26+theoretical+chemistry%22">Physical & theoretical chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Imidazoles%22">Imidazoles</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+compounds%22">Organic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Ketones%22">Ketones</searchLink><br /><searchLink fieldCode="DE" term="%22Hydantoin%22">Hydantoin</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: A simple and efficient methodology for the synthesis of 4,5-fused imidazolidin-2-ones from bicyclic and tricyclic ketones in a four-step sequence was described, by successive spirohydantoin Bucherer-Berg formation, mono- and dialkylation of the nitrogen atom of the hydantoin ring, regioselective reduction of one carbonyl function, and cationic cyclization associated with ring expansion. The key step of this sequential reaction was based on a tandem transposition/intramolecular amidoalkylation of cyclic spiro-N-acyliminium species. The process seems to be easy, general, regiospecific, resulted in the formation of polyheterocyclic systems containing an imidazolidin-2-one nucleus in good to excellent yields (67-99%), and is compatible with a large-scale production (up to 3 g of product 14, for example). Also, this method allows the preparation of the novel heterocycles 14 and 15 that have pharmaceutically interesting profiles, which are not accessible through short current synthetic methods. Finally, products 15 bear a secondary amide function crucial for further transformations, including the introduction of various pharmacophore groups either at the C or the N atoms of the imidazole ring. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1021/jo060616s Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 9 StartPage: 5303 Subjects: – SubjectFull: Physical & theoretical chemistry Type: general – SubjectFull: Imidazoles Type: general – SubjectFull: Organic compounds Type: general – SubjectFull: Ketones Type: general – SubjectFull: Hydantoin Type: general Titles: – TitleFull: General and Versatile Entry to 4,5-Fused Polycyclic Imidazolones Systems. Use of the Tandem Transposition/π-Cyclization of N-Acyliminium Species. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Anthony Pesquet – PersonEntity: Name: NameFull: Daïch, Adam – PersonEntity: Name: NameFull: van Hijfte, Luc IsPartOfRelationships: – BibEntity: Dates: – D: 07 M: 07 Text: 7/7/2006 Type: published Y: 2006 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 71 – Type: issue Value: 14 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
