Hekza-(2-Formil–5-Metoksifenoksi)Siklotrifosfazen’in Schiff Bazı Türevlerinin Sentezi ve Karakterizasyonu

Year 2014, Volume: 1 Issue: 3, 69 - 75, 28.12.2014

Furkan Özen , Kenan Koran , Fatih Aslan , Mustafa Arslan

Abstract

Hekzaklorosiklotrifosfazen (1) ile 2-hidroksi–4-metoksi benzaldehidin THF’de K₂CO₃ beraberliğinde oda sıcaklığında argon atmosferindeki reaksiyonundan hekza(2-formil-5-metoksifenoksi)siklotrifosfazen (2) elde edildi. Hekza(2-formil-5-metoksifenoksi)siklotrifosfazenin (2), 2-aminofenol, 4-aminobenzoikasit, 2-amino–5-metiltiazol, 4-aminobenzamit, 5-amino-1,3,4-tiazol-2-tiyol, 2-aminobenzotiazol, 4-aminofenol ve 4-aminoasetofenon ile reaksiyonundan Schiff bazı taşıyan fosfazen bileşikleri (3-10) sentezlendi. Elde edilen ürünlerin yapıları IR, NMR(¹H, ¹³C, ³¹P) ve elementel analiz ile aydınlatıldı. Hekza(2-formil-5-metoksifenoksi)siklotrifosfazen ile 2-amino–4-klorofenol ve 2-aminobenzimidazol’ün reaksiyonundan Schiff bazı elde edilemedi.

Keywords

Fosfazen, hekzaklorosiklotrifosfazen, Schiff bazı ve fosfazenler

Supporting Institution

TÜBİTAK

Project Number

107T407

Thanks

Bu çalışma TÜBİTAK‘ın 107T407’nolu BİDEP 1001 projesi kapsamında desteklenmiştir.

The Derivates Synthesis and Characterization of Some Schiff Base of Hexa-(2-Formyl–5-Methoxyphenoxy) Cyclotriphosphazene

Abstract

Hexa(2-formyl-5-methoxyphenoxy)cyclotriphosphazene (2) was obtained from the reaction of hexachlorocyclotriphosphazene (1) with 2-hydroxy-4-methoxybenzaldehyde in presence of K2CO3 at room temperature in THF under argon atmosphere. Schiff base containing phosphazene compounds (3-10) were synthesized by the reaction of hexa[(2-formyl-5-methoxy)phenoxy]cyclotriphosphazene (2) with 2-aminophenol, 4-aminobenzoicacid, 2-amino-5-methyl-1,3-thiazole, 4-aminobenzamide, 5-amino-1,3,4-thiazole-2-thiol, 2-aminobenzothiazole, 4-iminophenol and 4-iminoasetophenon respectively. The structures of the compounds were characterized by IR, 1H, 13C and 31P NMR spectroscopy and elemental analysis. Schiff base compounds could not be obtained from hexa[(2-formyl-5-methoxy)phenoxy]cyclotriphosphazene (2) with 2-amino-4-chlorophenol and 2-aminobenzimidazole.

Keywords

Phosphazene, hexachlorocyclotriphsophazene, Schiff base and phosphazenes

Project Number

107T407

References

• Allcock K. G., Shaw R. A. Ve Wells F. B. G., 1964, “Phosphorus-Nitrogen Compounds Part V. Friedel-Crafts Arylation of Hexachlorocyclotriphosphazatrien”, J. Chem. Soc., 121-130,
• Ozen, F., Cil, E., and Arslan, M., 2012, “Synthesis of Novel Oxime and Oxime Derivatives Phosphazenes from Hexachlorocyclotriphosphazene”, J.Chem.Soc.Pak., 34, 690-698.
• Koran, K., Ozkaya, A., Ozen, F., Cil, E., Arslan, M., 2013, “Synthesis, characterization, and biological evaluation of new oxime-phosphazenes”, Res Chem Intermed, 39, 1109-1124.
• Aslan, F., Demirpence, Z., Tatsiz, R., Türkmen, H., Oztürk, A.I., Arslan, M., 2008, “The Sythesis, Characterization and Photophysical Properties of Some New Cyclotriphosphazene Derivatives Bearing Schiff Base’’,Anorg. Allg. Chem., 634, 1140-1144.
• Çil, E. Arslan, M. Görgülü, A.O., 2006, “Synthesis of oxime bearing cyclophosphazenes and their reactions with alkyl and acyl halides”, Heteroatom Chemistry, 17 (2), 112-117.
• Gleria, M., and D. Jaeger R., 2001, “Aspects of Phosphazene Research”, Journal of Inorganic and Organometallic Polymers, 11, 1-45.
• Akmal S. Gaballa, Mohsen S. Asker, Atiat S. Barakat and Said M. Teleb, 2007, “Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from salicylaldehyde, 2-furaldehyde and phenylenediamine”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 67, 114-121.
• Rojo, G., Martin G., Lopez, F. A., Carriedo G. A., Alonso, F. J. G., Martinez J. I. F., 2000, “Second-Harmonic Response and Relaxation Behavior of High Glass-Transition Temparature Polyphosphazene Films”, Chem. Mater., 12, 3603-3610.
• Carriedo G. A., Alonso, F. J. G., Gonzalez P. A., 1997, “Improved Synthesis of Cyclic and Polymeric Phosphazenes Based on Facile Chlorine Substitution with Phenols Promoted by Cesium Carbonate”, Macromol. Rapid Commun., 18, 371-377.
• Diaz, C. V., Izquierdo, I. G., 1999, “Iron and Ruthenium Derivatives of Cyclophosphazenes Coordinated Through Nitrile Spacer Ligands”, Polyhedron, 18, 1479-1484.
• Carriedo G. A., Catuxo, L. F., Alonso, F. J. G., Elipe, P. G., Gonzalez P. A., 1996, “Preparation of a New Type of Phosphazene High Polymers Containing 2,2"-Dioxybiphenyl Groups”, Macromolacules, 16, 5320-5325.
• Carriedo G. A., Alonso, F. J. G., Gonzalez P. A., Alvarez, J. L. G., 1998, “Synthesis of New Phosphazene High Molecular Weight Polymers Containing Functionalized and Optically Active Spirocyclic Groups”, Macromolacules, 31, 10, 3189–3196.
• Çil, E., Arslan, M., Görgülü, A.O., 2006, “Synthesis and charecterization of benzyl and benzoyl substitueted oxime-phospazenes”, Polyhedron, 25, 3526–3532.
• Turgut Cin G., Odabaşoğlu M., Karaer H., 1999, “Preparation And Characterization Of Chromophor Group Containing Cyclotriphospahazenes: I Imino Chromophor Carrying Some Cyclotriphospahazenes”, Phosphorus, Sulfur and Silicon, 152, 9-25.