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

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-...

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Main Authors: Namburi Suresh, Gutta Lakshmi Prasanna, Mandava Venkata Basaveswara Rao, Manojit Pal
Format: Article
Language:English
Published: Elsevier 2019-12-01
Series:Arabian Journal of Chemistry
Online Access:http://www.sciencedirect.com/science/article/pii/S1878535216300636
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spelling doaj-90256298850c4616b503899dc27dd2fe2020-11-25T01:35:13ZengElsevierArabian 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
collection DOAJ
language English
format Article
sources DOAJ
author Namburi Suresh
Gutta Lakshmi Prasanna
Mandava Venkata Basaveswara Rao
Manojit Pal
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
author_facet Namburi Suresh
Gutta Lakshmi Prasanna
Mandava Venkata Basaveswara Rao
Manojit Pal
author_sort Namburi Suresh
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_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_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_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
publisher Elsevier
series Arabian Journal of Chemistry
issn 1878-5352
publishDate 2019-12-01
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
url http://www.sciencedirect.com/science/article/pii/S1878535216300636
work_keys_str_mv AT namburisuresh ultrasoundassistedsynthesisof6flavonylsubstituted14dihydrobenzod13oxazin2onesviasuzukimiyauracouplingunderpdccatalysis
AT guttalakshmiprasanna ultrasoundassistedsynthesisof6flavonylsubstituted14dihydrobenzod13oxazin2onesviasuzukimiyauracouplingunderpdccatalysis
AT mandavavenkatabasaveswararao ultrasoundassistedsynthesisof6flavonylsubstituted14dihydrobenzod13oxazin2onesviasuzukimiyauracouplingunderpdccatalysis
AT manojitpal ultrasoundassistedsynthesisof6flavonylsubstituted14dihydrobenzod13oxazin2onesviasuzukimiyauracouplingunderpdccatalysis
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