Synthesis of some benzo[d]thiazole derivatives via Suzuki cross-coupling reaction

Authors

  • Anh-Tuyet Vu Thi Lang Son Pedagogical College
  • Quoc-Hoan Duong Department of chemistry, Hanoi National University of Education, Ha Noi, Vietnam
  • Duc-Du Nguyen Hanoi Pedagogical University
  • Hien Nguyen Hanoi Pedagogical University
  • Trung-Hieu Nguyen Hanoi Pedagogical University
  • Dinh-Thang Duong Hanoi Pedagogical University 2

DOI:

https://doi.org/10.56764/hpu2.jos.2022.1.1.60-65

Abstract

In this study, 5 benzo[d]thiazole (3a-3e) derivatives were successfully synthesized in 2 steps through Suzuki cross-coupling reaction from 2-(4-bromophenyl)benzo[d]thiazole (2) and arylboronic acid derivatives with a fairly high yield of 80-95%.These compounds’ structure was determined through NMR and mass spectral analysis. Besides, The key compound 2 was synthesized  with a domestic microwave oven which helps to save cost and time in the synthesis process.

In this study, 5 benzo[d]thiazole (3a-3e) derivatives were successfully synthesized in 2 steps through Suzuki cross-coupling reaction from 2-(4-bromophenyl)benzo[d]thiazole (2) and arylboronic acid derivatives with a fairly high yield of 80-95%.These compounds’ structure was determined through NMR and mass spectral analysis. Besides, The key compound 2 was synthesized  with a domestic microwave oven which helps to save cost and time in the synthesis process.

References

Li, Y.; Mei, L.; Li, H.; et al. 2014, Predation of 2-methoxy-3-substituted-sulfonylamino-5-(2-acetamido-6-benzothiazole)-benzamide derivatives as antitumor agents, CN103772317.

Irfan, A.; Batool, F.; Naqvi, S. A.Z.; Islam, A.; Osman, S. M., Nocentini, A.; Alissa, S. A.; Supuran, C. T. (2020). Benzothiazole derivatives as anticancer agents, Journal of Enzyme Inhibition and Medicinal Chemistry, 35 (1), 265–279.

Haydon, D.J.; Czaplewski, L.G.; Palmer, N.J.; et al. (2012), Preparation of benzothiazole derivatives as antibacterial agents. US0004221.

Baum, J. S.; Chen, T. M. (1985), Benzothiazole derivatives for Plant growth and development Modification, Patent Number: 4,556,411.

Mahajan, D. P.; Bhosale, J. D.; Bendre, R. S. (2013), Synthesis, Characterization and Plant Growth Regulator Activity of Some Substituted 2-Amino Benzothiazole Derivatives, Journal of Applicable Chemistry, 2 (4): 765–771.

Šimonová, E.; Henselová, M.; Zahradník, P. (2005) Benzothiazole derivatives substituted in position 2as biologically active substances with plant growth regulation activity, Plant Soil Environ., 51, (11): 496–505.

Watanabe, H.; Ono, M.; Ariyoshi, T.; Katayanagi, R.; Saji, H. (2017), Novel Benzothiazole Derivatives as Fluorescent Probes for Detection of β‑Amyloid and α‑Synuclein Aggregates, ACS Chemical Neuroscience, 16, 8(8), 1656-1662.

Costa, S. P. G.; Batista, R. M. F.; Sousa, A. M. R. C.; Raposo, M. M. M. R. (2006), New Fluorescent Heterocyclic Materials: Synthesis, Solvatochromic and Fluorescence Properties, Materials Science Forum, 514-516, 147–151.

Mabrouk, A.; Azazi, A.; Alimi, K. (2010), On the properties of new benzothiazole derivatives for organic light emitting diodes (OLEDs): A comprehensive theoretical study, Journal of Physics and Chemistry of Solids, 71, 1225–1235.

Duong Quoc Hoan, Nguyen My Linh, Phan Thi Hoa, Hoang Thi Nhu Quynh, Vu Thi Anh Tuyet, (2018) Using a domestic microwave oven for synthesis of benzo[d]thiazole derivatives, J. Sci. HNUE, 63 (6), 127–135.

Dhayalan, V.; Hayashi, M. (2012), Synthesis of 2-Arylbenzothiazole Derivatives Based on Activated Carbon/Oxygen Oxidation Followed by Suzuki–Miyaura Coupling, Synthesis, 44, 2209–2216.

Published

31-08-2022

How to Cite

Vu Thi, A.-T., Duong, Q.-H., Nguyen, D.-D., Nguyen, H., Nguyen, T.-H., & Duong, D.-T. (2022). Synthesis of some benzo[d]thiazole derivatives via Suzuki cross-coupling reaction. HPU2 Journal of Science: Natural Sciences and Technology, 1(1), 60–65. https://doi.org/10.56764/hpu2.jos.2022.1.1.60-65

Volume and Issue

Section

Natural Sciences and Technology

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