Journals / Düzce Üniversitesi Bilim ve Teknoloji Dergisi / 2021 / Cilt: 9 - Sayı: 5

Ultrasound-Assisted One‐Pot Synthesis of 9-(Substituted heteroaryl) acridinedione Derivatives

Ultrases Destekli 9-(Substitue heteroaril) akridindion Türevlerinin Tek Basamakta Sentezi

Pages
1610–1620
Publication Date
2022-10-12
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)

Spectral analyses were accomplished by FTIR, 1H NMR, 13C NMR and LC-MS TOF analyses.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:An efficient green approach for the synthesis of 9-heteroaryl-acridine-1,8-dione derivatives (3a-f) was accomplished via reactions of dimedone (1) with various heteroaromatic aldehydes (2a-f) and ammonium acetate through one-pot multicomponent reactions in water under mild conditions using ultrasound irradiation in excellent yields.
📊
Key Findings & Data:Of the synthesized compounds, 3d-f were novel and this process presents the advantages of high yields and easy work-up procedures.
💡
Conclusion & Impact:Spectral analyses were accomplished by FTIR, 1H NMR, 13C NMR and LC-MS TOF analyses.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Çok bileşenli reaksiyonlar · Dihidropiridin · Heteroaromatik aldehitler

Abstract

An efficient green approach for the synthesis of 9-heteroaryl-acridine-1,8-dione derivatives (3a-f) was accomplished via reactions of dimedone (1) with various heteroaromatic aldehydes (2a-f) and ammonium acetate through one-pot multicomponent reactions in water under mild conditions using ultrasound irradiation in excellent yields. Of the synthesized compounds, 3d-f were novel and this process presents the advantages of high yields and easy work-up procedures. Spectral analyses were accomplished by FTIR, 1H NMR, 13C NMR and LC-MS TOF analyses.

Özet

Bu çalışma ile 9-heteroaril akridin-1,8-dion türevlerinin (3a-f) sentezi için yeşil kimya yaklaşımını benimseyen etkili bir yöntem geliştirilmiştir. Dimedon’un (1), çeşitli heteroaromatik aldehitlerle (2a-f) amonyum asetat kullanılarak sulu ortamda ve tek kapta ultrases dalgaları ile reaksiyonları gerçekleştirilmiştir. Bu yöntem ile ılıman koşullar altında, hedeflenen moleküller yüksek verimle elde edilmiştir. Ayrıca yöntemin kolay uygulanabilir olması ve deney sonrası işlemlerinin son derece basit olması en önemli çalışma avantajlarındandır. Sentezlenen bileşiklerden 3d-f orijinal moleküller olup, elde edilen tüm ürünlerin karakterizasyonları FTIR, 1H NMR, 13C NMR ve LC-MS TOF analizleri kullanılarak gerçekleştirilmiştir.

🔖

Cite This Article

BAYRAMOĞLU, D., YAKUT, M. (2022). Ultrasound-Assisted One‐Pot Synthesis of 9-(Substituted heteroaryl) acridinedione Derivatives. Düzce Üniversitesi Bilim ve Teknoloji Dergisi, Cilt: 9 - Sayı: 5, 1610–1620. https://ajindex.com/articles/493886

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (1)

  1. Á. Magyar and Z. Hell, “An efficient one-pot four-component synthesis of 9-aryl hexahydroacridine-1,8-dione derivatives in the presence of a molecular sieves supported iron catalyst,” Catalysis Letters, vol. 149, no. 9, p. 2528-34, 2019. [2] A. Velena, N. Zarkovic, K. Gall Troselj, E. Bisenieks, A. Krauze, J. Poikans, et al., “1,4-dihydropyridine derivatives: dihydronicotinamide analogues—model compounds targeting oxidative stress,” Oxidative medicine and cellular longevity, vol. 2016, p. 35, 2016, Article ID 1892412. [3] D. J. Triggle, “Calcium channel antagonists: clinical uses—past, present and future,” Biochemical pharmacology, vol 74, no.1, p. 1-9, 2007. [4] R. Mannhold, B. Jablonka, W. Voigt, K. Schoenafinger, E. Schraven, “Calcium-and calmodulin-antagonism of elnadipine derivatives: comparative SAR,” European journal of medicinal chemistry, vol. 27, no. 3, p. 229-35, 1992. [5] N. Edraki, A. R. Mehdipour, M. Khoshneviszadeh, R. Miri, “Dihydropyridines: evaluation of their current and future pharmacological applications,” Drug Discovery Today, vol. 14, no. 21-22, p. 1058-66, 2009. [6] A. Shafiee, R. Miri, A. Dehpour, F. Soleymani, “Synthesis and calcium‐channel antagonist activity of Nifedipine analogues containing nitroimidazolyl substituent in guinea‐pig ileal smooth muscle,” Pharmacy and Pharmacology Communications, vol. 2, no. 11, p. 541-3, 1996. [7] F. Pourmorad, F. Hadizadeh, A.S hafiee, “Synthesis and calcium‐channel antagonist activity of 4‐imidazolyl‐1,4‐dihydropyridines,” Pharmacy and Pharmacology Communications, vol. 3, no.4, p.165-8, 1997. [8] I. Antonini, P. Polucci, A. Magnano, S. Martelli, “Synthesis, antitumor cytotoxicity, and DNA-binding of novel N-5,2-di(ω-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamides,” Journal of medicinal chemistry, vol 44. no. 20, p. 3329-33, 2001. [9] A. Albert, “The acridines: their preparation, physical, chemical, and biological properties and uses,” Edward Arnold, London, 1966. [10] P. Murugan, P. Shanmugasundaram, V. Ramakrishnan, B. Venkatachalapathy, N. Srividya, P. Ramamurthy, et al. “Synthesis and laser properties of 9-alkyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives,” Journal of the Chemical Society, Perkin Transactions 2, vol. 4, p.999-1004, 1998. [11] P. Shanmugasundaram, P. Murugan, V.T. Ramakrishnan, N. Srividya, P. Ramamurthy, “Synthesis of acridinedione derivatives as laser dyes,” Heteroatom Chemistry, vol.7, no. 1, p 17-22, 1996. [12] R