BAZI YENİ N-ASETİLPİRAZOLİNLERİN BENZİLOKSİFENİL ESASLI SENTEZLERİ

Abstract

Sübstitüe benziloksifenil kalkonlar, 1a-j, hidrazin hidrat (2) ve glasiyal asetik asit (3) ile 2-metoksietanol çözücüsü içinde reaksiyona girdiğinde 4a-j ile belirtilen yeni sübstitüe N-asetilpirazolinler elde edildi. Yeni elde edilen N-asetilpirazolinler FT-IR, 1H-NMR, GC-MS ve elementel analiz ile karakterize edildi.

Keywords

• -

Benzyloxyphenyl based synthesis of some novel N-acetylpyrazolines

Abstract

Substituted benzyloxyphenyl chalcones 1a-j on reaction with hydrazine hydrate 2 and glacial acetic acid 3 in 2-methoxyethanol as reaction medium give novel substituted N-acetylpyrazolines 4a-j. Newly obtained N-acetyl pyrazolines characterized on the basis of IR, ¹H-NMR, GC-MS and elemental analysis.

Keywords

• Benzyloxyphenyl chalcones
• N-acetylpyrazolines
• 2-methoxyethanol.

References

1. Turan-Zitouni G, Özdemir A, Kaplancikli ZA, Chevallet P, Tunali Y. Synthesis and Antimicrobial Activities of Some 1-[(N, N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines. Phosphorus, Sulfur, and Silicon and the Related Elements. 2005 Dec;180(12):2717–24.
2. Ozdemir A, Turan-Zitouni G, Kaplancikli Z. Novel analogues of 2-pyrazoline: synthesis, characterization, and antimycobacterial evaluation. Turk J Chem. 2008;32:529–38.
3. Nugent RA, Murphy M, Schlachter ST, Dunn CJ, Smith RJ, Staite ND, et al. Pyrazoline bisphosphonate esters as novel antiinflammatory and antiarthritic agents. Journal of Medicinal Chemistry. 1993 Jan;36(1):134–9.
4. Manna F, Chimenti F, Bolasco A, Cenicola M, D’Amico M, Parrillo C, et al. Anti-inflammatory, analgesic and antipyretic N-acetyl-Δ2-pyrazolines and dihydrothienocoumarines. European Journal of Medicinal Chemistry. 1992 Sep;27(6):633–9.
5. Rajendra Prasad Y, Lakshmana Rao A, Prasoona L, Murali K, Ravi Kumar P. Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines. Bioorganic & Medicinal Chemistry Letters. 2005 Nov;15(22):5030–4.
6. Zhang XH, Wu SK, Gao ZQ, Lee CS, Lee ST, Kwong H-L. Pyrazoline derivatives for blue color emitter in organic electroluminescent devices. Thin Solid Films. 2000 Aug;371(1-2):40–6.
7. Hasan A, Abbas A, Akhtar M. Synthesis, characterization and fluorescent property evaluation of 1,3,5-triaryl-2-pyrazolines. Molecules. 2011;16:7789–802.
8. Beliak I, Kravets V, Kryuchin A. Luminescence of the pyrazoline dye in nanostructured zeolite matriх. Phys Quantum Electron Optoelectron. 2007;20:33–5.

9. Raiford LC, Peterson WJ. Identification of phenylhydrazones and isomeric pyrazolines obtained from chalcones. The Journal of Organic Chemistry. 1937 Jan;1(6):544–51.
10. Kidwai M, Misra P. Ring Closure Reactions of Chalcones Using Microwave Technology. Synthetic Communications. 1999 Sep;29(18):3237–50.
11. Zangade S, Shinde A, Patil A, Vibhute Y. An efficient and facile ring closure of 2’-hydroxychalcones under irradiation of tungsten light. European Journal of Chemistry. 2012 Jun 30;3(2):208–10.
12. Li J-T, Zhang X-H, Lin Z-P. An improved synthesis of 1,3,5-triaryl-2-pyrazolines in acetic acid aqueous solution under ultrasound irradiation. Beilstein Journal of Organic Chemistry. 2007;3(1):13.
13. Kapoor KK, Ganai BA, Kumar S, Andotra CS. KHSO4• H2O/SiO2 ‐Catalyzed, One‐Pot, Solvent‐Free Synthesis of Pyrazolines, Tetrahydrocarbozoles and Indoles using Microwave Irradiation. Synthetic Communications. 2006 Sep;36(18):2727–35.
14. Atir R, Mallouk S, Bougrin K, Soufiaoui M, Laghzizil A. Porous Calcium Hydroxyapatite as an Efficient Catalyst for Synthesis of Pyrazolines via 1,3‐Dipolar Cycoloaddition Under Solvent‐Free Microwave Irradiation. Synthetic Communications. 2006 Feb;36(1):111–20.
15. Lokanatha Rai KM, Linganna N. Mercuric Acetate in Organic Synthesis: A Simple Procedure for the Synthesis of Pyrazolines 1. Synthetic Communications. 1997 Nov;27(21):3737–44.
16. Azarifar D, Maleki B. Microwave‐Assisted Aromatization of 1,3,5‐Trisubstituted 2‐Pyrazolines by Bi(NO3)3 • 5H2O, as a Novel and Convenient Oxidizing Agent. Synthetic Communications. 2005 Oct;35(19):2581–5.
17. Alex K, Tillack A, Schwarz N, Beller M. Zinc-Catalyzed Synthesis of Pyrazolines and Pyrazoles via Hydrohydrazination. Organic Letters. 2008 Jun;10(12):2377–9.
18. Fazaeli R, Aliyan H, Mallakpour S, Rafiee Z, Bordbar M. Tungstophosphoric Acid Supported on Highly Organosoluble Polyamide (PW12/PA): Highly Efficient Catalysts for the Synthesis of Novel 1,3,5-Triaryl-2-pyrazoline Derivatives. Chinese Journal of Catalysis. 2011 Jan;32(3-4):582–8.
19. Krishna PR, Sekhar ER, Mongin F. Lewis acid- and/or Lewis base-catalyzed [3+2] cycloaddition reaction: synthesis of pyrazoles and pyrazolines. Tetrahedron Letters. 2008 Nov;49(48):6768–72.
20. Zangade SB, Mokle SS, Shinde AT, Vibhute YB. An atom efficient, green synthesis of 2-pyrazoline derivatives under solvent-free conditions using grinding technique. Green Chemistry Letters and Reviews. 2013 Jun;6(2):123–7.