Synthesis of 1,3-Bis-Pyrazole Derivatives

Korkmaz Yurtoğlu E., Zora M.

Anatolian Conference on Organic Chemistry (ACOC4), Antalya, Türkiye, 4 - 07 Mart 2024, ss.54

  • Yayın Türü: Bildiri / Tam Metin Bildiri
  • Basıldığı Şehir: Antalya
  • Basıldığı Ülke: Türkiye
  • Sayfa Sayıları: ss.54
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Synthesis of 1,3-Bis-Pyrazole Derivatives

Esra Korkmaz, Metin Zora

Middle East Technical University, Department of Chemistry, 06800 Ankara, Türkiye

Email: ekorkmaz@metu.edu.tr

Pyrazoles are a significant class of nitrogen-containing five membered heterocycles. They form a primary position in the design and synthesis of novel biologically active agents.1 They exhibit a wide range of biological properties such as analgesic, antibacterial, antidepressant, anti-inflammatory activities.1 In particular, bis-pyrazoles have a gaining interest in therapeutic chemistry because of their diverse biological activities.2 Notably, they are playing an essential role in the medicinal chemistry, showing anticancer, anti-inflammatory, antimicrobial activities.2 Although pyrazoles have been intensely studied for over a century, there still exists a great demand to develop new methodologies for their synthesis. Therefore, the synthesis of bis-pyrazole molecules have been attracted by organic chemists.1,2

In this study, our aim is to synthesize 1,3-bis-pyrazole derivatives 3. We have found that 1,9-diarylnona-2,7-diyne-1,9-diones (1) are convenient intermediates for the synthesis of 1,3-bis-pyrazole derivatives 3 since, when treated with hydrazines 2, they undergo first conjugate addition followed by cyclization to afford the corresponding 1,3-bis(1,5-diaryl-1H-pyrazol-3-yl)propane derivatives 3. Therefore, starting compounds 1 will be first synthesized by employing Sonogashira cross-coupling reactions and then their reactions will be explored.

 

Figure 1. Synthesis of 1,3-bis-pyrazole derivatives 3.

 

References:

  1. (a) Zora, M.; Kivrak, A.; Yazici, C. J. Org. Chem. 2011, 76, 6726-6742. (b) Zora, M.; Kivrak, A. J. Org. Chem. 2011, 76, 9379−9390. (c) Zora, M.; Demirci, D.; Kivrak, A.; Kelgokmen, Y. Tetrahedron Lett. 2016, 57, 993-997.

2.     Danne, A. B.; Deshpande, M. V.; Sangshetti, J. N.; Khedkar, V. M.; Shingate, B. B. ACS Omega 2021, 6, 24879-24890.