Abstract
The demand for a cleaner environment has led chemists to develop greener protocols, notably by using catalysts. Encapsulation of an active substance on a solid support makes the process of separation of the catalyst much simpler, thereby generating minimal waste. We report herein the preparation of a novel basic catalyst, 3-methylaminopropyl-functionalized Fe3O4 nanoparticles (Fe3O4@MAP nanoparticles), which catalyzes the one-pot synthesis of [1,3]oxazine derivatives under ultrasonic conditions. Advantages include mild reaction condition, easy catalyst recovery and recyclability, shorter reaction time and use of green solvents. We also found that one derivative, 2-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine, suppresses the toxic effect caused by the chlorpyrifos pesticide on the blood cells of Polypedates teraiensis tadpoles.
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Abbreviations
- Fe3O4@MAP:
-
Ferrite@(3-methylaminopropyl)silyl
- FTIR:
-
Fourier transform infrared spectroscopy
- CDCl3 :
-
Deuterated chloroform
- DMSO-d6 :
-
Deuterated dimethyl sulfoxide
- 1H-NMR:
-
Proton nuclear magnetic resonance spectroscopy
- 13C-NMR:
-
Carbon nuclear magnetic resonance spectroscopy
- TMS:
-
Tetramethylsilane
- XRD:
-
X-ray diffraction
- TEM:
-
Transmission electron microscopy
- EDS:
-
Energy-dispersive X-ray spectroscopy
- TLC:
-
Thin-layer chromatography
- ESI–MS:
-
Electrospray ionization mass spectrometry
- TGA:
-
Thermogravimetric analysis
- VSM:
-
Vibrating sample magnetometry
- RBC:
-
Red blood corpuscles
- SEM:
-
Scanning electron microscopy
- MAPTMS:
-
(3-Methylaminopropyl)trimethoxysilane
References
Afradi M, Foroughifar N, Pasdar H, Moghanian H (2016) <scp > l</scp > -proline N-sulfonic acid-functionalized magnetic nanoparticles: a novel and magnetically reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidine-2-(1H)-thiones under solvent-free conditions. RSC Adv 6:59343–59351. https://doi.org/10.1039/C6RA10558K
Bremner DH (1994) Recent advances in organic synthesis utilizing ultrasound. Ultrason Sonochem 1:S119–S124. https://doi.org/10.1016/1350-4177(94)90009-4
Chylińska JB, Urbański T, Mordarski M (1963) Dihydro-1,3-oxazine derivatives and their antitumor activity. J Med Chem 6:484–487. https://doi.org/10.1021/jm00341a004
Chylińska JB, Janowiec M, Urbański T (1971) Antibacterial activity of dihydro-1,3-oxazine derivatives condensed with aromatic rings in positions 5,6. Br J Pharmacol 43:649–657. https://doi.org/10.1111/j.1476-5381.1971.tb07194.x
Cocuzza AJ, Chidester DR, Cordova BC et al (2001) Synthesis and evaluation of efavirenz (Sustiva™) analogues as HIV-1 reverse transcriptase inhibitors: replacement of the cyclopropylacetylene side chain. Bioorganic Med Chem Lett 11:1177–1179. https://doi.org/10.1016/S0960-894X(01)00192-5
Coleman RJ, Quinn NP, Traub M, Marsden CD (1990) Nasogastric and intravenous infusions of (+)-4-propyl-9-hydroxynaphthoxazine (PHNO) in Parkinson’s disease. J Neurol Neurosurg Psychiatry 53:102–105
de Benneville PL, Luskin LS (1959) Oxazine and oxazoline polymers. US2897182A
Deb N, Das S (2013) Chlorpyrifos toxicity in fish: a review. Curr World Environ 8:77–84. https://doi.org/10.12944/CWE.8.1.17
Dhakane VD, Gholap SS, Deshmukh UP et al (2014) An efficient and green method for the synthesis of [1,3]oxazine derivatives catalyzed by thiamine hydrochloride (VB1) in water. C R Chim 17:431–436. https://doi.org/10.1016/j.crci.2013.06.002
Gupta S, Khanna G, Khurana JM (2016) A facile eco-friendly approach for the one-pot synthesis of 3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-diones using glycerol as a green media. Environ Chem Lett 14:559–564. https://doi.org/10.1007/s10311-016-0570-6
Joyce JN, Presgraves S, Renish L et al (2003) Neuroprotective effects of the novel D3/D2 receptor agonist and antiparkinson agent, S32504, in vitro against 1-methyl-4- phenylpyridinium (MPP +) and in vivo against 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine (MPTP): a comparison to ropinirole. Exp Neurol 184:393–407. https://doi.org/10.1016/S0014-4886(03)00353-4
Kajino M, Shibouta Y, Nishikawa K, Meguro K (1991) Synthesis and biological activities of new 2-substituted 1,4-benzoxazine derivatives. Chem Pharm Bull (Tokyo) 39:2896–2905. https://doi.org/10.1248/cpb.39.2896
Katsura Y, Nishino S, Takasugi H (1991) Studies on antiulcer drugs. I. Synthesis and antiulcer activities of imidazo(1,2-a)pyridinyl-2-oxobenzoxazolidines-3-oxo-2H-1,4-benzoxazines and related compounds. Chem Pharm Bull (Tokyo) 39:2937–2943. https://doi.org/10.1248/cpb.39.2937
Khaligh NG (2013) Ultrasonics sonochemistry ultrasound-assisted one-pot synthesis of substituted coumarins catalyzed by poly (4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst. Ultrason Sonochem 20:1062–1068. https://doi.org/10.1016/j.ultsonch.2013.01.001
Krishna G, Makoto H (2000) In vivo rodent micronucleus assay: protocol, conduct and data interpretation. Mutat Res Mol Mech Mutagen 455:155–166. https://doi.org/10.1016/S0027-5107(00)00117-2
Laurent S, Forge D, Port M et al (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications (vol 108, pg 2064, 2008). Chem Rev 108:2064–2110. https://doi.org/10.1021/Cr900197g
Maharajan A, Narayanasamy Y, Ganapiriya V, Shanmugavel K (2015) Histological alterations of a combination of Chlorpyrifos and Cypermethrin (Nurocombi) insecticide in the fresh water crab, Paratelphusa jacquemontii (Rathbun). J Basic Appl Zool 72:104–112. https://doi.org/10.1016/j.jobaz.2015.08.002
Mukhopadhyay C, Rana S, Butcher RJ (2010) An ionic liquid [secbmim] + Br—as a “dual reagent catalyst” for the multicomponent synthesis of (quinolinyl- and isoquinolinyl- amino) alkylnaphthols, their bis-analogs and a facile route to naphthoxazines. Arkivoc 2010:291–304
Nongrum R, Nongthombam GS, Kharkongor M et al (2016) A nano-organo catalyzed route towards the efficient synthesis of benzo[b]pyran derivatives under ultrasonic irradiation. RSC Adv 6:108384–108392. https://doi.org/10.1039/C6RA24108E
Postek M, Howard K, Johnson A, McMichael K (1980) Scanning electron microscopy. Ladd Research Industries 83 Holly Court Williston, Vermont 05495
Tang Z, Zhu Z, Xia Z et al (2012) Synthesis and fungicidal activity of novel 2,3-disubstituted-1,3-benzoxazines. Molecules 17:8174–8185. https://doi.org/10.3390/molecules17078174
Tomasulo M, Raymo FM, Gables C (2010) Use of oxazine compounds for making chromogenic materials. US 2010/0249403 A1
Zhang P, Terefenko EA, Fensome A et al (2002) Potent nonsteroidal progesterone receptor agonists: synthesis and SAR study of 6-aryl benzoxazines. Bioorganic Med Chem Lett 12:787–790. https://doi.org/10.1016/S0960-894X(02)00025-2
Acknowledgements
R. Nongrum would like to thank Sankardev College, Shillong, and UGC for the award of teacher fellowship under the Faculty Development Programme. R. Nongkhlaw acknowledges DST for financial support (EEQ/2016/00646). The analytical assistance from the Department of Chemistry—NEHU, SAIF—NEHU, Department of Nanotechnology—NEHU, CDRI—Lucknow, and IIT—Guwahati, is highly acknowledged.
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Nongrum, R., Kharkongor, M., Nongthombam, G.S. et al. [1,3]oxazines: green synthesis by sonication using a magnetically-separable basic nano-catalyst and investigation of its activity against the toxic effect of a pesticide on the morphology of blood cells. Environ Chem Lett 17, 1325–1331 (2019). https://doi.org/10.1007/s10311-019-00857-1
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DOI: https://doi.org/10.1007/s10311-019-00857-1