Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions.
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| Title: | Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions. |
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| Authors: | Panday, Anoop Kumar1, Mishra, Richa1, Jana, Asim1, Parvin, Tasneem2 tasneem@nitp.ac.in, Choudhury, Lokman H.1 lokman.iitp@gmail.com |
| Source: | Journal of Organic Chemistry. 4/6/2018, Vol. 83 Issue 7, p3624-3632. 9p. |
| Abstract: | Herein, we report two novel methods for the synthesis of pyrimidine fused quinolines using a one-pot C-C and C-N bond forming strategy from the reaction of 6-aminouracils with 2-bromobenzaldehydes or 2-bromobenzyl bromide derivatives in the presence of 10 mol % CuCl2 without using any ligand. The reaction of 2-bromobenzaldehyde or its derivatives with 6-aminouracils in the presence of K2CO3 as base and a catalytic amount of CuCl2 in DMF medium under microwave heating conditions provides corresponding pyrimidine fused quinoline derivatives in good yields within 30 min. Alternatively, pyrimidine fused quinoline derivatives have been synthesized from the reaction of 2-bromobenzyl bromides with 6-aminouracil derivatives in the presence of molecular oxygen, CuCl2 (10 mol %), and K2CO3 as base in DMF under reflux conditions. Structures of all the products were unambiguously confirmed by spectroscopic techniques and by recording single crystal XRD of 3a. [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: 129019748 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Panday%2C+Anoop+Kumar%22">Panday, Anoop Kumar</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Mishra%2C+Richa%22">Mishra, Richa</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Jana%2C+Asim%22">Jana, Asim</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Parvin%2C+Tasneem%22">Parvin, Tasneem</searchLink><relatesTo>2</relatesTo><i> tasneem@nitp.ac.in</i><br /><searchLink fieldCode="AR" term="%22Choudhury%2C+Lokman+H%2E%22">Choudhury, Lokman H.</searchLink><relatesTo>1</relatesTo><i> lokman.iitp@gmail.com</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 4/6/2018, Vol. 83 Issue 7, p3624-3632. 9p. – Name: Abstract Label: Abstract Group: Ab Data: Herein, we report two novel methods for the synthesis of pyrimidine fused quinolines using a one-pot C-C and C-N bond forming strategy from the reaction of 6-aminouracils with 2-bromobenzaldehydes or 2-bromobenzyl bromide derivatives in the presence of 10 mol % CuCl2 without using any ligand. The reaction of 2-bromobenzaldehyde or its derivatives with 6-aminouracils in the presence of K2CO3 as base and a catalytic amount of CuCl2 in DMF medium under microwave heating conditions provides corresponding pyrimidine fused quinoline derivatives in good yields within 30 min. Alternatively, pyrimidine fused quinoline derivatives have been synthesized from the reaction of 2-bromobenzyl bromides with 6-aminouracil derivatives in the presence of molecular oxygen, CuCl2 (10 mol %), and K2CO3 as base in DMF under reflux conditions. Structures of all the products were unambiguously confirmed by spectroscopic techniques and by recording single crystal XRD of 3a. [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/acs.joc.7b03272 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 9 StartPage: 3624 Titles: – TitleFull: Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Panday, Anoop Kumar – PersonEntity: Name: NameFull: Mishra, Richa – PersonEntity: Name: NameFull: Jana, Asim – PersonEntity: Name: NameFull: Parvin, Tasneem – PersonEntity: Name: NameFull: Choudhury, Lokman H. IsPartOfRelationships: – BibEntity: Dates: – D: 06 M: 04 Text: 4/6/2018 Type: published Y: 2018 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 83 – Type: issue Value: 7 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
