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

Namburi Suresh; Gutta Lakshmi Prasanna; Mandava Venkata Basaveswara Rao; Manojit Pal

Arabian Journal of Chemistry (Dec 2019)

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

Namburi Suresh,
Gutta Lakshmi Prasanna,
Mandava Venkata Basaveswara Rao,
Manojit Pal

Affiliations

Namburi Suresh: Department of Chemistry, Krishna University, Krishna Dist., Andhra Pradesh, India
Gutta Lakshmi Prasanna: Department of Chemistry, Krishna University, Krishna Dist., Andhra Pradesh, India
Mandava Venkata Basaveswara Rao: Department of Chemistry, Krishna University, Krishna Dist., Andhra Pradesh, India; Corresponding author. Tel.: +91 40 6657 1500.
Manojit Pal: Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India; Corresponding author. Tel.: +91 40 6657 1500.

Journal volume & issue: Vol. 12, no. 8
pp. 4220 – 4230

Abstract

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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

Published in Arabian Journal of Chemistry

ISSN: 1878-5352 (Print)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: http://www.journals.elsevier.com/arabian-journal-of-chemistry/

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