Vol 62 No 2 (2017): Journal of the Chilean Chemical Society
Original Research Papers
Published
June 16, 2017
How to Cite
Bustamante, S. E., & Rivas, B. L. (2017). NEW SYNTHESIS METHOD TO OBTAIN A METHACRYLIC MONOMER WITH A PYRYLIUM GROUP. Journal of the Chilean Chemical Society, 62(2). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/205
Copyright (c) 2017 Saúl E. Bustamante, Bernabé L. Rivas
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Abstract
Methacrylic monomers with pyrylium salt derivatives are widely used to detect nucleophilic species. A new synthesis method has been used to obtain a
pyrylium salt that is trisubstituted with phenyl groups at positions 2,4, and 6. The phenyl group of the 4-position has a metacrylate group in the para-position. The
new synthesis method implies the esterification of 4-hydroxybenzaldehyde, using methacrylic anhydride. The formed compound react with acetophenone to form
the pyrylium derivative. The yields of both reactions are greater than those previously reported in the literature.
References
- Balaban, A. T. Aromaticity of six-membered rings with one heteroatom. Top. Heterocycl. Chem. 2, 1–44 (2008).
- Balaban, A. T. et al. Pyrylium Salts: Syntheses, Reactions, and Physical Properties (1204 Literaturzitate). Adv. Heterocycl. Chem. Suppl. 2, (1982).
- Sawada, G. A. et al. Chalcogenopyrylium dyes as inhibitors/modulators of P-glycoprotein in multidrug-resistant cells. Bioorg. Med. Chem.16, 9745–9756 (2008).
- Okamoto, T. & Yamamoto, Nobuko Kawaguchi, M. Pharmaceutical compositions containing pyrylium compounds, pyrylium salts and process for manufacturing a medicament containing the aforesaid compounds. 1–30 (2000).
- Rao, B. A., Lee, J.-Y. & Son, Y.-A. Synthesis of a novel pyrylium salt with chemoselectivity to a cyanide anion. Supremol. Chem.27, 191–200 (2015).
- Santamaria, J. & Valdes, C. Six-Membered Rings with One Oxygen: Pyrylium Ion, Related Systems and Benzo-Derivatives. Mod. Heterocycl. Chem. 1631–1682 (2011).
- Heidarizadeh, F. & Abadast, F. Reactions of some nucleophiles with pyrylium salts. Orient. J. Chem. 27, 1421 (2011).
- Ampliación de Química Orgánica Avanzada. Capítulo 7. Heterociclos Aromáticos de seis Miembros con Oxígeno 1–8 Available at: https://riuma.uma.es/xmlui/bitstream/handle/10630/7518/Tema_7.Heterociclos_aromaticos_con_oxigeno.pdf?sequence=1. (Accessed: 27th April 2017).
- Milov, A. A., Starikov, A. G., Gridin, M. K. & Minyaev, R. M. Effect of the counterion on the steric and electronic structure of pyrylium cation. Russ. J. Gen. Chem. 77, 1373–1385 (2007).
- Bhowmik, P. K., Burchett, R. A., Han, H. & Cebe, J. J. Synthesis and characterization of poly (pyridinium salt) s with organic counterion exhibiting both lyotropic liquid-crystalline and light-emitting properties. J. Polym. Sci. Part A Polym. Chem.39, 2710–2715 (2001).
- Ruiz Guerrero, R. et al. Catalytic synthesis of 1, 3, 5-triphenylbenzenes, β -methylchalcones and 2, 4, 6-triphenyl pyrylium salts, promoted by a super acid triflouromethane sulfonic clay from acetophenones. J. Mex. Chem. Soc. 50, 114–118 (2006).
- Harmsen, S. et al. Rational design of a chalcogenopyrylium-based surface-enhanced resonance Raman scattering nanoprobe with attomolar sensitivity. Nat. Commun.6, (2015).
- Wang, L. et al. Conjugated poly (pyridinium salt) s as fluorescence lightup probes for heparin sensing. J. Appl. Polym. Sci.131, (2014).
- Joule, J. A. & Mills, K. Heterocyclic chemistry. (John Wiley & Sons, 2008).
- Balaban, A. T. 8.1 Balaban--Nenitzescu--Praill Reaction. Six-Membered Heterocycles 402 (2011).
- Franconetti, A., Contreras-Bernal, L. & Cabrera-Escribano, F. From Pyrylium to Pyridinium Salts: Understanding Physicochemical Features. in Proceedings of The 17th International Electronic Conference on Synthetic Organic Chemistry (2013).
- García, F. et al. Pyrylium-containing polymers as sensory materials for the colorimetric sensing of cyanide in water. Chem. Commun. 2790–2792 (2005).
- Acosta, B. G. Sensores químicos cromogénicos y fluorogénicos para la detección de iones y moléculas neutras. (Universidad Politécnica de Valencia, 2007).
- San José Pascual, N. Síntesis de polímeros que incorporan sistemas receptores de aniones: estudio de sus aplicaciones como dosímetros y sensores. (Universidad de Burgos, 2007).
- Naveau, H. P. Infrared, NMR and mass spectra of the methacrylates or methacrylate-anhydride of five phenolic compounds. Spectrochim. Acta Part A Mol. Spectrosc. 28, 651–658 (1972).
- Grabowski, Z. R., Rotkiewicz, K. & Rettig, W. Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures. Chem. Rev.103, 3899–4032 (2003).
