Solid‐Solid Phase and Solvent‐Free Oxidative Removal of<i>N</i>‐(4‐Alkoxyphenyl) Groups of Monocyclic β‐Lactams with Ceric Ammonium Nitrate as a Cheap, Simple, and Efficient Method

Jarrahpour, Aliasghar; Zarei, Maaroof

doi:10.1080/00397910801981326

Cited by 11 publications

(3 citation statements)

References 29 publications

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“…Among these methods, oxidative cleavage by ceric ammonium nitrate (CAN) of p-alkoxyphenyl moiety attached to the nitrogen of the β-lactam ring offers the most direct synthesis of N-unsubstituted β-lactams (Jarrahpour, et al, 2008).…”

Section: D-mentioning

confidence: 99%

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

et al. 2015

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In the title compound, C15H11ClN2O4, the central β-lactam ring is approximately planar [maximum deviation = 0.044 (2) Å for the N atom from the mean plane] and subtends dihedral angles of 61.17 (11) and 40.21 (12) °, respectively, with the nitro and chlorobenzene rings. Both substituents lie to the same side of the β-lactam core. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [010]. The chains are cross-linked by C—H⋯O and weak C—H⋯π interactions, generating a three-dimensional network. The solvent molecules were found to be highly disordered and their contribution to the scattering was removed with the SQUEEZE procedure in PLATON [Spek (2009 ▸). Acta Cryst. D65, 148–155], which indicated a solvent cavity of volume 318 Å3 containing approximately 114 electrons. These solvent molecules are not considered in the given chemical formula and other crystal data.

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Section: D-mentioning

confidence: 99%

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

et al. 2015

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“…The solvent-free reaction or solid-state reactions are green methods in organic synthesis which have numerous advantages: reduced pollution, low cost and simplicity in process and handling (Tanaka and Toda, 2000;Mikami, 2005). Mechanochemistry can be as simple as grinding two reactants in a mortar and pestle or more complex, as with the use of commercially available ball mills (Schmeyers et al, 1998;Jarrahour and Zarei, 2008). Schiff base ligands contain some heteroatoms such as nitrogen, sulphur and oxygen which affords it the ability to form complexes as these atoms have affinity for transition metals such as copper, manganese, chromium, iron, cobalt, nickel, etc.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free Synthesis and Characterization of Cu(II), Co(II) and Ni(II) Complexes of 2-(3-phenylallylidene) thiosemicarbazide

Aguzue¹,

Oviawe

Olajide³

et al. 2021

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Mechanochemical solvent-free synthesis of Cu, Co and Ni complexes of 2-(3-phenylallylidene) thiosemicarbazide is described. The mechanochemical products were characterized on the basis of solubility, melting point, conductivity, FTIR, UV-Visible, GC-MS, 1H-NMR and 13C-NMR. The Schiff base ligand and its metal (II) complexes are coloured stable compounds. The solubility test shows that the compounds are soluble in dimethylsulphoxide, dimethexylformamide; partially soluble in ethanol and insoluble in water. The melting points of the compounds were within the range of 179 oC to 183 oC. The UV-Visible electronic spectra data showed the different transfers and transitions in the ligand and metal complexes. The different absorptions in the electronic spectra also predicted the possible structures of the complexes. The 13C-NMR and 1H-NMR showed the different carbon and hydrogen environments in the ligand. The GCMS confirmed the structure of the ligand and exhibited different fragments. The antimicrobial activities of the ligand were enhanced with the metal complexes and the results were very interesting as the complexes showed good antifungal and antibacterial activities.

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“…[13][14][15] CAN has proved to be a very useful oxidant in synthetic organic chemistry over four decades. [16][17][18] The solubility of CAN in non-polar organic solvents is very low, and hence CAN-mediated reactions must be performed in polar organic solvents or mixable water-organic solvents such as acetonitrile and require cold conditions and a tedious workup using ethyl acetate. Also, the solubility of some organic compounds in mixed acetonitrile-water is low.…”

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confidence: 99%

Cerium(IV) Tetrabutylammonium Nitrate (CTAN): A Mild and Efficient N-dearylation Agent for Synthesis of N-unsubstituted 2-azetidinones

Zarei

2017

Journal of Chemical Research

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A simple and efficient protocol for the conversion of N-p-methoxyphenyl, N-p-ethoxyphenyl, N-p-methoxynaphthyl, N-3,4-dimethoxybenzyl and N-p-methoxybenzyl-2-azetidinones to N-unsubstituted 2-azetidinones using cerium(IV) tetrabutylammonium nitrate (CTAN) in dichloromethane is described. The method is compatible with a number of functional groups, and N-unsubstituted 2-azetidinones can be prepared under mild conditions at room temperature. The reaction is rapid, and pure products are obtained in good yields.

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Solid‐Solid Phase and Solvent‐Free Oxidative Removal ofN‐(4‐Alkoxyphenyl) Groups of Monocyclic β‐Lactams with Ceric Ammonium Nitrate as a Cheap, Simple, and Efficient Method

Cited by 11 publications

References 29 publications

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

Solvent-free Synthesis and Characterization of Cu(II), Co(II) and Ni(II) Complexes of 2-(3-phenylallylidene) thiosemicarbazide

Cerium(IV) Tetrabutylammonium Nitrate (CTAN): A Mild and Efficient N-dearylation Agent for Synthesis of N-unsubstituted 2-azetidinones

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