Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis
Pd/C facilitated Suzuki–Miyaura coupling of 2-aryl-3-bromoflavones with 4,4-disubstituted (1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acids under ultrasound irradiation. The methodology involving the use of 10%Pd/C-TBAB-K2CO3 system in DMF/H2O afforded corresponding 6-flavonyl substituted 1,4-...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2019-12-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535216300636 |
| _version_ | 1818150966600400896 |
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| author | Namburi Suresh Gutta Lakshmi Prasanna Mandava Venkata Basaveswara Rao Manojit Pal |
| author_facet | Namburi Suresh Gutta Lakshmi Prasanna Mandava Venkata Basaveswara Rao Manojit Pal |
| author_sort | Namburi Suresh |
| collection | DOAJ |
| description | Pd/C facilitated Suzuki–Miyaura coupling of 2-aryl-3-bromoflavones with 4,4-disubstituted (1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acids under ultrasound irradiation. The methodology involving the use of 10%Pd/C-TBAB-K2CO3 system in DMF/H2O afforded corresponding 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones in good yield within a short reaction time. The role of ultrasound and catalyst along with the recyclability of Pd/C was examined and a reaction mechanism is proposed. Keywords: Pd/C, Ultrasound, Suzuki–Miyaura coupling, Flavones, Benzoxazin-2-one |
| first_indexed | 2024-12-11T13:31:20Z |
| format | Article |
| id | doaj.art-90256298850c4616b503899dc27dd2fe |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-11T13:31:20Z |
| publishDate | 2019-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-90256298850c4616b503899dc27dd2fe2022-12-22T01:05:15ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112842204230Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysisNamburi Suresh0Gutta Lakshmi Prasanna1Mandava Venkata Basaveswara Rao2Manojit Pal3Department of Chemistry, Krishna University, Krishna Dist., Andhra Pradesh, IndiaDepartment of Chemistry, Krishna University, Krishna Dist., Andhra Pradesh, IndiaDepartment of Chemistry, Krishna University, Krishna Dist., Andhra Pradesh, India; Corresponding author. Tel.: +91 40 6657 1500.Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India; Corresponding author. Tel.: +91 40 6657 1500.Pd/C facilitated Suzuki–Miyaura coupling of 2-aryl-3-bromoflavones with 4,4-disubstituted (1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acids under ultrasound irradiation. The methodology involving the use of 10%Pd/C-TBAB-K2CO3 system in DMF/H2O afforded corresponding 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones in good yield within a short reaction time. The role of ultrasound and catalyst along with the recyclability of Pd/C was examined and a reaction mechanism is proposed. Keywords: Pd/C, Ultrasound, Suzuki–Miyaura coupling, Flavones, Benzoxazin-2-onehttp://www.sciencedirect.com/science/article/pii/S1878535216300636 |
| spellingShingle | Namburi Suresh Gutta Lakshmi Prasanna Mandava Venkata Basaveswara Rao Manojit Pal Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis Arabian Journal of Chemistry |
| title | Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis |
| title_full | Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis |
| title_fullStr | Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis |
| title_full_unstemmed | Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis |
| title_short | Ultrasound assisted synthesis of 6-flavonyl substituted 1,4-dihydro-benzo[d][1,3]oxazin-2-ones via Suzuki–Miyaura coupling under Pd/C catalysis |
| title_sort | ultrasound assisted synthesis of 6 flavonyl substituted 1 4 dihydro benzo d 1 3 oxazin 2 ones via suzuki miyaura coupling under pd c catalysis |
| url | http://www.sciencedirect.com/science/article/pii/S1878535216300636 |
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