Fast method for synthesis of alkyl and aryl-N-methylnitrones

Molecules

Volumn 16, Issue 8, 2011, Pages 6677-6683

  Yavuz, Serkan ^a   Ozkan, Hamdi ^b   Colak, Naki ^c   Yildirir, Yilmaz ^a  

^a GAZI UNIVERSITY   (Turkey)

^b CANKIRI KARATEKIN UNIVERSITY   (Turkey)

^c HITIT UNIVERSITY   (Turkey)

Author keywords

Grinding; Nitrone; Solid phase synthesis; Solventless

Indexed keywords

NITROGEN OXIDE; NITRONES;

CHEMISTRY; ORGANIC CHEMISTRY; PROCEDURES; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TIME FACTOR; TRANSITION TEMPERATURE;

CHEMISTRY, ORGANIC; NITROGEN OXIDES; PROTON MAGNETIC RESONANCE SPECTROSCOPY; TIME FACTORS; TRANSITION TEMPERATURE;

EID: 80052256103     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16086677     Document Type: Article

References (19)

1. Black, D.S.C.; Crozier, R.F.; Davis, V.C. 1,3-Dipolar cycloaddition reactions of nitrones. Synthesis 1975, 1975, 205-221.
2. Dondas, H.A.; Cummins, J.E.; Grigg, R.; Thornton, P.M. X=Y-ZH Systems as potential 1,3-dipoles. Part 53: Sequential nucleophilic ring opening-1,3-dipolar cycloaddition reactions of Z-oxime anions with aziridines and dipolarophiles. Tetrahedron 2001, 57, 7951-7961.
3. Alibes, R.; Blanco, P.; de March, P.; Figueredo, M.; Font, J.; Alvarez-Larena, A.; Piniella, J.F. Synthesis and 1,3-dipolar cycloadditions of a new enantiopure cyclic nitrone. Tetrahedron Lett. 2002, 44, 523-525.
4. Kumar, K.R.R.; Mallesha, H.; Rangappa, K.S. Synthesis of novel isoxazolidine derivatives and studies for their antifungal properties. Eur. J. Med. Chem. 2003, 38, 613-619. (Pubitemid 36775362)
5. Gothelf, K.V.; Jorgenson, K.A. Asymmetric 1,3-Dipolar cycloaddition reactions Chem. Rev. 1998, 98, 863-909. (Pubitemid 128631444)
6. Broggini, G.; Zecchi, G. Pyrrolizidine and indolizidine syntheses involving 1,3-Dipolar cycloadditions. Synthesis 1999, 1999, 905-917. (Pubitemid 29266227)
7. Mulzer, J. Organic Synthesis Highlights; Verlag Chemie: Weinheim, Germany, 1991; pp. 3-4.
8. Huisgen, R.; Grashey, R.; Sauer, J. The Chemistry of Alkenes; Wiley Interscience: London, UK, 1964; pp. 806-807.
9. Tania, R.A.; Gareth, W.V.C.; Colin, L.R. Benign approaches for the synthesis of bis-imine schiff bases. Green Chem. 2006, 8, 50-53.
10. Kumar, S.; Sharma, P.; Kapoor, K.K.; Hundal, M.S. An efficient, catalyst- and solvent-free, four component, and one-pot synthesis of polyhydroquinolines on grinding. Tetrahedron 2008, 64, 536-542. (Pubitemid 350192544)
11. Longhi, K.; Moreira, D.N.; Marzari, M.R.B.; Floss, V.M.; Bonacorso, H.G.; Zanatta, N.; Martins, M.A.P. An efficient solvent-free synthesis of NH-pyrazoles from β-dimethylaminovinylketones and hydrazine on grinding. Tetrahedron Lett. 2010, 51, 3193-3196.
12. Heravi, M.M.; Poormohammad, N.; Beheshtiha, Y.S.; Baghernejad, B. Efficient synthesis of 2,4-Disubstituted thiazoles under grinding. Synth. Commun. 2011, 41, 579-582.
13. Andrade, M.M.; Barros, M.T.; Pinto, R.C. Exploiting microwave-assisted neat procedures: Synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines. Tetrahedron 2008, 64, 10521-10530.
14. Bigdeli, M.A.; Nikje, M.M.A. An efficient and rapid chemoselelective synthesis of α-aryl-N-methylnitrones in dry media. Monatsh. Chem. 2001, 132, 1547-1549.
15. Nikje, M.M.A.; Bigdeli, M.A. A microwave assistedoxidation of benzaldehydes under solvent-free condition usingoxone/wet-alumina. Phosphorus Sulfur Silicon Relat Elem. 2004, 179, 1445-1448. (Pubitemid 38998007)
16. Colacino, E.; Nun, P.; Colacino, F.M.; Martinez, J.; Lamaty, F. Solvent-free synthesis of nitrones in a ball-mill. Tetrahedron 2008, 64, 5569-5576.
17. Colonna, S.; Piront, V.; Carrea, G.; Pasta, P.; Zambianchi, F. Oxidation of secondary amines by molecular oxygen and cyclohexanone monooxygenase. Tetrahedron 2004, 60, 569-575. (Pubitemid 38045364)
18. Coutouli, A.E.; Malamidou, X.E.; Stampelos, X.N.; Alexopoulou, I.N. Formation and reduction reactions of 3-indol-3-yl-isoxazolidines. Tetrahedron 1997, 53, 707-718. (Pubitemid 26423015)
19. Cummins, H.C.; Coates, R.M. α-Oxygenation of aldehydes and cyclic ketones by acylation & arrangement of nitrones. J. Org. Chem. 1983, 48, 2070-2076.