Green Synthesis of MgO Nanoparticles Using Caesalpinia Sappan Seeds and their Application for Direct Conversion of Alcohol to Azide
DOI:
https://doi.org/10.18311/jmmf/2022/32012Keywords:
Caesalpinia Sappan, Green Synthesis, MgO NPs, ADMP and Amino Alkyl Azide.Abstract
Azides have been considered as one of the energy rich functional groups as they are prominent precursors for reactive species like nitrenes and nitrenium ions. Also, they were utilized in synthesis of triazoles, triazolines and triazenes. The present work reports an eco- friendly synthesis of MgO NPs by utilizing Caesalpinia Sappan seeds as a novel fuel by solution combustion method. Multiple characterization techniques encompassing FTIR, UV- visible, XRD and SEM were used to study physico-chemical properties of synthesized MgO NPs. A convenient synthesis of amino alcohol via mixed anhydride method was carried out in the first step. Further, amino alkyl azide has been synthesized under mild condition by using the green synthesized MgO nanoparticles as a catalyst along with the addition of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate, a safe, stable and efficient diazo transfer reagent. Structures of newly synthesized compounds were well characterized by HRMS, Proton and C-13 analysis techniques.
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References
Hiroki Tanimoto et al., (2013): Recent Applications and Developments of Organic Azides in Total Synthesis of Natural Products. Natural Product Communications. Vol. 8 No 7, pp.1021-1034. DOI: https://doi.org/10.1177/1934578X1300800730
Dayun Huang et al., (2017): Recent Advances in Reactions of Azides. Advanced synthesis and catalysis. DOI: https://doi.org/10.1002/adsc.201700103
Stefan Brase et al., (2005): Organic Azides: An Exploding Diversity of a Unique Class of Compounds Angewandte. Chemie International edition. 44, pp.5188 – 5240. DOI: https://doi.org/10.1002/anie.200400657
Liu.Q. et al., (2003): Simple conversion of aromatic amines into azides. organic letters. Vol. 5, No. 14, pp. 2571-2572 DOI: https://doi.org/10.1021/ol034919+
Hughes.D.L. et al., (1988): A mechanistic study of the Mitsunobu esterification reaction .Journal of the American Chemical Society. 110, 19, pp.6487–6491. DOI: https://doi.org/10.1021/ja00227a032
Alexander Breuning et al., (2003): An improved synthesis of aziridine-2,3- dicarboxylates via azido alcohols – Epimerization studies. Tetrahedron Asymmetry 14(21), pp.3301-3312. DOI: https://doi.org/10.1016/j.tetasy.2003.09.015
Takashi Kouko . et al., (2005): Total synthesis of marine bisindole alkaloids, (+)- hamacanthins A, B and (–)-antipode of cis-dihydrohamacanthin B. Tetrahedron Volume 61, Issue 9 ,pp. 2309-2318. DOI: https://doi.org/10.1016/j.tet.2005.01.058
Shuji Yamashita et al., (2011): Total Synthesis of Cortistatins A and J. The Journal of Organic Chemistry 76, 8, pp.2408–2425. DOI: https://doi.org/10.1021/jo2002616
Pronin. S.V. et al., (2010): Synthesis of Streptolydigin, a Potent Bacterial RNA Polymerase Inhibitor. Journal of the American Chemical Society 132, 41, pp.14394–14396. DOI: https://doi.org/10.1021/ja107190w
Irene de Migue et al., (2012): Intramolecular Azide-Alkene 1,3-Dipolar Cycloaddition/Enamine Addition(s) Cascade Reaction: Synthesis of Nitrogen-Containing Heterocycles. Advanced synthesis and catalysis. volume 354, Issue 9, pp. 1731-1736 DOI: https://doi.org/10.1002/adsc.201200071
Pilar M. Fresneda et al., (2004): Application of Iminophosphorane-Based Methodologies for the Synthesis of Natural Products. Synlett. No. 1, pp. 0001– 001705.01.200. DOI: https://doi.org/10.1055/s-2003-43338
Margaret L Wong et al., (2012): An Asymmetric Synthesis of L-Pyrrolysine, Organic. Letters, 14, 6, pp.1378–1381. DOI: https://doi.org/10.1021/ol300045c
Nakahara K et al., (2011) Asymmetric total synthesis of clavolonine. Organic Letters 13(8), pp.2015-2017. DOI: https://doi.org/10.1021/ol200376z
Tobias muller et al., (2012) Cicindeloine from Stenus cicindeloides – Isolation, Structure Elucidation, and Total Synthesis. European Journal of Organic Chemistry,. pp. 2323–2330. DOI: https://doi.org/10.1002/ejoc.201101709
Mitsuru Kitamura et al., (2010): Direct Synthesis of Organic Azides from Alcohols Using 2-Azido-1,3-dimethylimidazolinium Hexafluoro-phosphate. Synlett 23(9), pp. 1335- 1338. DOI: https://doi.org/10.1055/s-0031-1290958
Mitsuru Kitamura et al., (2012): Direct Synthesis of Organic Azides from Primary Amines with 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate. European journal of organic chemistry. 458–462. DOI: https://doi.org/10.1002/ejoc.201001509
Abinaya.S. et al., (2021): Green synthesis of magnesium oxide nanoparticles and its applications: A review. Sustainable Chemistry and Pharmacy.19, pp. 100368. DOI: https://doi.org/10.1016/j.scp.2020.100368
Harshal Dabhane et al., (2021): MgO nanoparticles: synthesis, characterization, and applications of a catalyst for organic transformations. European journal of chemistry 12(1), pp. 86-108. DOI: https://doi.org/10.5155/eurjchem.12.1.86-108.2060