Journals / Turkish Journal of Chemistry / 2020 / Cilt: 44 - Sayı: 5

Synthesis and characterization of piperazine-substituted dihydrofuran derivatives viaMn(OAc)3 mediated radical cyclizations

Pages
1303–1313
Publication Date
2022-11-01
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

In addition, dihydrofuran-piperazine compounds 3h-j and 3k-n were prepared at low to medium yields (20%–40%) from the reactions of 1e-g with 2a and 1e-h with 2c, respectively.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The aim of this study is to synthesize novel piperazine-containing dihydrofuran compounds (3a-n)from radical additions and cyclizations of diacyl and alkyl-acyl piperazine derivatives (1a-h) with 1,3-dicarbonyl compounds (2a-c) mediated by $Mn(OAc)_3$ for the first time.
📊
Key Findings & Data:From the reactions of 1a-c with dimedone (2a);1a, 1c, and 1d with acetylacetone (2b); and 1a with ethylacetoacetate(2c) ,the dihydrofuran-piperazine compounds 3a-c, 3d-f, and 3g were obtained in medium to high yields (31%–81%), respectively.
💡
Conclusion & Impact:In addition, dihydrofuran-piperazine compounds 3h-j and 3k-n were prepared at low to medium yields (20%–40%) from the reactions of 1e-g with 2a and 1e-h with 2c, respectively.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

The aim of this study is to synthesize novel piperazine-containing dihydrofuran compounds (3a-n)from radical additions and cyclizations of diacyl and alkyl-acyl piperazine derivatives (1a-h) with 1,3-dicarbonyl compounds (2a-c) mediated by $Mn(OAc)_3$ for the first time. From the reactions of 1a-c with dimedone (2a);1a, 1c, and 1d with acetylacetone (2b); and 1a with ethylacetoacetate(2c) ,the dihydrofuran-piperazine compounds 3a-c, 3d-f, and 3g were obtained in medium to high yields (31%–81%), respectively. In addition, dihydrofuran-piperazine compounds 3h-j and 3k-n were prepared at low to medium yields (20%–40%) from the reactions of 1e-g with 2a and 1e-h with 2c, respectively.

🔖

Cite This Article

SARI, S., YILMAZ, M. (2022). Synthesis and characterization of piperazine-substituted dihydrofuran derivatives viaMn(OAc)3 mediated radical cyclizations. Turkish Journal of Chemistry, Cilt: 44 - Sayı: 5, 1303–1313. https://ajindex.com/articles/601581

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (11)

  1. Dua R, Shrivastava S, Sonwane SK, Shrivastava SK. Pharmacological Significance of Synthetic Heterocycles Scaffold: A Review.Advances in Biological Research 2011;5: 120-144
  2. Rachakonda V, Alla M, Kotipalli SS, Ummani R. Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents. European Journal of Medicinal Chemistry 2013; 70: 536-547
  3. Szabo M, Herenbrink CK, Christopoulos A, Lane JR, Capuano B. Structure−Activity Relationships of Privileged Structures Lead to the Discovery of Novel Biased Ligands at the Dopamine D2 Receptor. Journal of Medicinal Chemistry2014; 57: 4924−4939
  4. Chaudhary P, Kumar R, Verma AK, Singh D, Yadav V, et al. Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives. Bioorganic and Medicinal Chemistry2006; 14: 1819-1826
  5. Harish KP, Mohana KN, Mallesha L, Kumar BNP. Synthesis of novel 1-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-piperazine derivatives and evaluation of their in vivo anticonvulsant activity.European Journal of Medicinal Chemistry 2013; 65: 276-283
  6. Patel KN, Telvekar VN. Design, synthesis and antitubercular evaluation of novel series of N-[4-(piperazin-1-yl)phenyl]cinnamamide derivatives. European Journal of Medicinal Chemistry 2014; 75: 43-56
  7. Wang T, Kadow JF, Zhang Z, Yin Z, Gao Q, et al. Inhibitors of HIV-1 attachment. Part 4: A study of the effect of piperazine substitution patterns on antiviral potency in the context of indole-based derivatives. Bioorganic and Medicinal Chemistry Letters 2009; 19: 5140-5145
  8. Tuğrak M, Gül HI, Bandow K, Sakagami H, Gülçin I, et al. Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors. Bioorganic Chemistry 2019; 90: 103095
  9. Meena P, Nemaysh V, Khatri M, Manral A, Luthra PM, et al. Synthesis, biological evaluation and molecular docking study of novel piperidine and piperazine derivatives as multi-targeted agents to treat Alzheimer’s disease. Bioorganic and Medicinal Chemistry 2015; 23: 1135-1148
  10. Piemontese L, Tomás D, Hiremathad A, Capriati Vi, Candeias E, et al. Donepezil structurebased hybrids as potential multifunctional antiAlzheimer’s drug candidates. Journal of Enzyme Inhibition and Medicinal Chemistry 2018;33: 1212-1224
  11. Stegmeier F, Warmuth M, Sellers WR, Dorsch M. Targeted Cancer Therapies in the Twenty-First Century: Lessons From Imatinib. Cli