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Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu

Year 2019, Issue: 16, 242 - 246, 31.08.2019
https://doi.org/10.31590/ejosat.558597

Abstract

Bu çalışmada; polimerleşme ve
metal kompleksi oluşturabilme özelliklerine sahip amin türevi; üç yeni monomer sentezlenmiştir.
 Sentez reaksiyonu olarak, petasis
reaksiyonu seçilmiştir. Uygun optimizasyon koşullarında, herhangi bir katalizör
kullanılmadan ve oldukça yüksek verimlerle hedef ürünler(monomer) elde
edilmiştir. Reaksiyon verimine; sıcaklık, çözücü, atmosfer koşullarının yanısıra,
substitüentlerin de etkili olduğu görülmüştür. Özellikle elektron salıcı
substitüent içeren yapıların elektron çekici substitüent içeren bileşiklere göre
daha istemli olduğu ve veriminin de yüksek olduğu görülmüştür. Alkilaminofenol
bileşik sınıfına ait olan bu monomerlerin yapısal analizleri ise 1H-NMR
ve 13C-NMR ile tamamlanmıştır. Sentezi yapılan monomerler, moleküler
baskılanmış polimer olarak biyomoleküler tanımada kullanılabilir. Bu durum; bir
çok hedef molekül için onları tanıyan uygun materyallerin  elde edilmesi anlamına gelmektedir. Çalışma
bu yönüyle oldukça önemlidir. 

Supporting Institution

Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Birimi

Project Number

ÖAP(F)-2018/2

Thanks

Bu çalışma Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Birimi tarafından ÖAP(F)-2018/2 nolu proje ile desteklenmiştir.

References

  • Candeias N.R., Montalbano F., Cal P. M. S. D., Gois P. M. P.(2010). Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction. Chemical Review. 110, 6169–6193.
  • Han W. Y., Zuo J., Zhang X. M., Yuan W. C. (2013). Enantioselective Petasis reaction among salicylaldehydes, amines, and organoboronic acids catalyzed by BINOL. Tetrahedron, 69, 537-541.
  • Kaboudin B, Zangooei A., Kazemi F., Yokomatsu T.(2018). Catalyst-free Petasis-type reaction: Three-component decarboxylative coupling of boronic acids with proline and salicylaldehyde for the synthesis of alkylaminophenols. Tetrahedron Letters, 59, 1046-1049.
  • Koolmeister T., Sodergren M., Scobie M. (2002). Pinacolyl boronic esters as components in the Petasis reaction. Tetrahedron Letters, 43, 5965–596.
  • Kozioz A., Grzeszczyk B., Koziozn A., Staszewska-Krajewska O., Furman B., Chmielewski M. (2010). Ferrier-Petasis Rearrangement of 4-(Vinyloxy)azetidin-2-ones: An Entry to Carbapenams and Carbacephams. Journal of Organic Chemistry, 75, 6990–6993.
  • Lou S., Schaus S. E. (2008). Asymmetric Petasis Reactions Catalyzed by Chiral Biphenols. Journal of American Chemical Society, 130, 6922–6923.
  • Mandai H., Murota K., Suga S. (2012). Studies On The Petasis Reaction Of 2-Pyridişnecarbaldehyde Derivatives And Its Products. Heterocycles, 85(7), 1655 – 1669.
  • Petasis N.A., Akritopoulou I. (1993). The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines. Tetrahedron Letters, 34, 583-586.
  • Schlienger N., Bryce M. R., Hansen T. K. (2000). Heterocyclic aldehydes as novel components in the boronic Mannich reaction. Tetrahedron Letters ,41, 1303–1305.
  • Shi X., Kiesman W. F., Levina A., Xin Z. (2013).Catalytic Asymmetric Petasis Reactions of Vinylboronates. Journal of Organic Chemistry, 78, 9415−942.
  • Tao Z., Junping W., Jianli H., Qiliang D., Shuo W. (2017). One-step post-imprint modification achieve dual-function of glycoprotein fluorescent sensor by "Click Chemistry. Biosensors and Bioelectronics, 91, 756–761.
  • Wang O., Finn M. G. (2000). 2H-Chromenes from Salicylaldehydes by a Catalytic Petasis Reaction. Organic Letters, 2(25), 4063–4065.
  • Wang J., Shen Q., Zhang j., Song G. (2015). Metal-free multicomponent coupling reaction of aliphatic amines, formaldehyde, organoboronic acids, and propiolic acids for the synthesis of diverse propargylamines. Tetrahedron Letters, 56, 903–906.
  • Wei J., Ni Y., Zhang W., Zhang Z., Zhang J. (2017). Detection of glycoprotein through fluorescent boronic acid-based molecularly imprinted polymer . Analytica Chimica Acta, 960 110-116
  • Yan H., Row H. K. (2006). Charecteristic and Synthetic Approach of Molecularly Imprinted Polymer. Journal of Molecular Sciences, 7, 155-178.
  • Ying L., Limin W., Yuanyuan S., Jianjun Y. (2010). Solvent-free Synthesis of Alkylaminophenols via Petasis Boronic Mannich Reaction in One Pot without Catalysts. Chinese Journal of Chemistry, 28, 2039-2044.

Synthesis and Characterization of Amine Derivative Monomers to be used in Preparing Smart Materials

Year 2019, Issue: 16, 242 - 246, 31.08.2019
https://doi.org/10.31590/ejosat.558597

Abstract

In this study, amine derivative three new monomers forming polymer and metal complex synthesized. As the synthesis reaction, the petasis reaction was chosen. Under optimization conditions, target products (monomer) were obtained without any catalyst and with very high yields. Some parameters, such as temperature, solvent, atmospheric conditions, and substituents, has affected reaction yields.In particular, it observed that the structures containing the electron release substituent were more eager than the compounds containing the electron acceptor and the yield was high. Structural analyses of monomers of the alkylaminophenol class were made with 1H-NMR and 13C-NMR. The synthesized monomers can use as molecular printed polymers in biomolecular recognition. That means to obtain suitable materials for synthesized of target molecules. Therefore, this aspect of the study is important.

Project Number

ÖAP(F)-2018/2

References

  • Candeias N.R., Montalbano F., Cal P. M. S. D., Gois P. M. P.(2010). Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction. Chemical Review. 110, 6169–6193.
  • Han W. Y., Zuo J., Zhang X. M., Yuan W. C. (2013). Enantioselective Petasis reaction among salicylaldehydes, amines, and organoboronic acids catalyzed by BINOL. Tetrahedron, 69, 537-541.
  • Kaboudin B, Zangooei A., Kazemi F., Yokomatsu T.(2018). Catalyst-free Petasis-type reaction: Three-component decarboxylative coupling of boronic acids with proline and salicylaldehyde for the synthesis of alkylaminophenols. Tetrahedron Letters, 59, 1046-1049.
  • Koolmeister T., Sodergren M., Scobie M. (2002). Pinacolyl boronic esters as components in the Petasis reaction. Tetrahedron Letters, 43, 5965–596.
  • Kozioz A., Grzeszczyk B., Koziozn A., Staszewska-Krajewska O., Furman B., Chmielewski M. (2010). Ferrier-Petasis Rearrangement of 4-(Vinyloxy)azetidin-2-ones: An Entry to Carbapenams and Carbacephams. Journal of Organic Chemistry, 75, 6990–6993.
  • Lou S., Schaus S. E. (2008). Asymmetric Petasis Reactions Catalyzed by Chiral Biphenols. Journal of American Chemical Society, 130, 6922–6923.
  • Mandai H., Murota K., Suga S. (2012). Studies On The Petasis Reaction Of 2-Pyridişnecarbaldehyde Derivatives And Its Products. Heterocycles, 85(7), 1655 – 1669.
  • Petasis N.A., Akritopoulou I. (1993). The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines. Tetrahedron Letters, 34, 583-586.
  • Schlienger N., Bryce M. R., Hansen T. K. (2000). Heterocyclic aldehydes as novel components in the boronic Mannich reaction. Tetrahedron Letters ,41, 1303–1305.
  • Shi X., Kiesman W. F., Levina A., Xin Z. (2013).Catalytic Asymmetric Petasis Reactions of Vinylboronates. Journal of Organic Chemistry, 78, 9415−942.
  • Tao Z., Junping W., Jianli H., Qiliang D., Shuo W. (2017). One-step post-imprint modification achieve dual-function of glycoprotein fluorescent sensor by "Click Chemistry. Biosensors and Bioelectronics, 91, 756–761.
  • Wang O., Finn M. G. (2000). 2H-Chromenes from Salicylaldehydes by a Catalytic Petasis Reaction. Organic Letters, 2(25), 4063–4065.
  • Wang J., Shen Q., Zhang j., Song G. (2015). Metal-free multicomponent coupling reaction of aliphatic amines, formaldehyde, organoboronic acids, and propiolic acids for the synthesis of diverse propargylamines. Tetrahedron Letters, 56, 903–906.
  • Wei J., Ni Y., Zhang W., Zhang Z., Zhang J. (2017). Detection of glycoprotein through fluorescent boronic acid-based molecularly imprinted polymer . Analytica Chimica Acta, 960 110-116
  • Yan H., Row H. K. (2006). Charecteristic and Synthetic Approach of Molecularly Imprinted Polymer. Journal of Molecular Sciences, 7, 155-178.
  • Ying L., Limin W., Yuanyuan S., Jianjun Y. (2010). Solvent-free Synthesis of Alkylaminophenols via Petasis Boronic Mannich Reaction in One Pot without Catalysts. Chinese Journal of Chemistry, 28, 2039-2044.
There are 16 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Yeliz Ulaş 0000-0003-2038-1851

Project Number ÖAP(F)-2018/2
Publication Date August 31, 2019
Published in Issue Year 2019 Issue: 16

Cite

APA Ulaş, Y. (2019). Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. Avrupa Bilim Ve Teknoloji Dergisi(16), 242-246. https://doi.org/10.31590/ejosat.558597