Aminimides IX. A general synthesis of 1‐substituted‐2‐imidazolidinones

A novel mode of SmI2 activation has been developed using ureates as reaction promoters. Several ureates formed by treatment of the corresponding ureas with n-BuLi have been shown to activate SmI2 to a substantial extent toward the reduction of 1-chlorodecane. Complexes formed from SmI2 and various ureates have been shown to be useful for the reduction of a variety of organohalides, including substrates of low reactivity such as aryl fluorides. Because of ease of synthesis and low molecular weight, the conjugate base of triethylurea (TEU(-)) was of primary focus. Visible spectroscopy and reactivity data are consistent with the hypothesis that the same complex is being formed when SmI2 is combined with either 2 or 4 equiv of TEU(-), in spite of the greater reactivity of SmI2/4 TEU(-) with some alkyl halides. We propose that the active reductant is an N,O chelate formed between SmI2 and 2 equiv of TEU(-).

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“…Distillation (0.5 mmHg, 186–190 °C) yielded 2.54 g (69%) of the title compound 7a as a white solid, mp 39–40 °C (lit . 36–39 °C).…”

Section: Methodsmentioning

confidence: 99%

“…Distillation (0.5 mmHg, 186−190 °C) yielded 2.54 g (69%) of the title compound 7a as a white solid, mp 39−40 °C (lit. 68 N-iso-Propylpropylene Urea (7c). Distillation (0.9 mmHg, 199− 202 °C) yielded 2.46 g (67%) of the title compound 7c as a white solid, mp 151−152 °C (lit.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

The Use of Ureates as Activators for Samarium Diiodide

et al. 2016

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“…The compounds under study are intermediate products in the synthesis of azetidinone, dihydroquinolone, benzodiazepine, imidazole, and dihydropyrimidinedione derivatives [4][5][6][7][8].In this paper we report a synthesis of 1-aryl-substituted tetrahydropyridones from N-aryl-β-alanines. The extensive interest has been focused on the influence of substituents as well as on the number, attachment position, and the nature of the substituents.…”

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confidence: 99%

“…The compounds under study are intermediate products in the synthesis of azetidinone, dihydroquinolone, benzodiazepine, imidazole, and dihydropyrimidinedione derivatives [4][5][6][7][8]. The compounds under study are intermediate products in the synthesis of azetidinone, dihydroquinolone, benzodiazepine, imidazole, and dihydropyrimidinedione derivatives [4][5][6][7][8].…”

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confidence: 99%

Synthesis and Structure Elucidation of 1-Aryl-substituted Tetrahydropyridone Derivatives

Mickevičius

Vaickelionienė

Mikulskiene³

et al. 2005

Chem Heterocycl Compd

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spectroscopy. The extensive interest has been focused on the influence of substituents as well as on the number, attachment position, and the nature of the substituents. The unknown shielding of the heterocyclic ring on the aromatic carbon atoms was determined and the averaged chemical shift increments were successfully used for the assignment of the aromatic moiety of the studied compounds. The presence of two chiral elements in compounds 16, 17, 20-21 resulted in the mixture of diastereomers and double sets of the resonances in NMR spectra.Keywords: N-aryl-β-alanines, tetrahydropyridones, NMR spectroscopy.N-Aryl-β-alanines and their derivatives possess a wide spectrum of biological activity [1-3]. The compounds under study are intermediate products in the synthesis of azetidinone, dihydroquinolone, benzodiazepine, imidazole, and dihydropyrimidinedione derivatives [4][5][6][7][8].In this paper we report a synthesis of 1-aryl-substituted tetrahydropyridones from N-aryl-β-alanines. N-Aryl-β-alanines 1-12 were used as starting compounds. These compounds were obtained from the corresponding arylamines and unsaturated acids by the method previously developed in our laboratory [5,7].1-Aryl-3-ethoxycarbonyl-1,4,5,6-tetrahydro-4(1H)-pyridones 13-21 and 3-acetyl-1-aryl-1,4,5,6tetrahydro-4(1H)-pyridones 22-24 were prepared from the corresponding N-aryl-β-alanines and ethyl acetoacetate or 2,4-pentanedione in refluxing toluene in the presence of a catalytic amount of hydrochloric acid. It is possible that condensation of NH group in β-alanine with 1,3-diketo compound takes place first, and then the intermediate compound undergoes cyclization resulting in the respective hydropyridone 13-24. The yield of the target compounds was not high, however the formed products were crystalline substances and were obtained from the reaction mixture easily.The products obtained were analyzed by NMR spectroscopy. The NMR spectral assignments have been made by the comparison of the spectra between themselves and with the related fragments, assuming the validity of the additivity of the substituent effects, their general characteristics and the signal intensities [9-10]. __________________________________________________________________________________________

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“…e, R' = C-R II NH (5,113), sulfonic acids (47b) (91), and phosphonic acids (47c) (91), imido chlorides (47d) (144), and nitriles (47e) (148) into the corresponding aminimides (47).…”

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confidence: 99%

Chemistry of Aminimides

Wawzonek¹

1980

Ind. Eng. Chem. Prod. Res. Dev.

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The period 1972-1979 saw considerable activity in research of the chemistry and utilization of aminimides. Studies have extended investigation to aminimides in which the acyl group is derived from imino acids, cyanuric acid, phosphonic acids, and picric acid and to vinylogues of aminimides. Work continued with aminimides derived from nitrogen heterocycles and their conversion to diazepines and bridged nitrogen bicyclic compounds. Commercial utilization of aminimides based on 1,1dimethylhydrazine has been hampered in this country by the loss of the sole commercial source of this compound.

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Aminimides IX. A general synthesis of 1‐substituted‐2‐imidazolidinones

Cited by 10 publications

References 6 publications

The Use of Ureates as Activators for Samarium Diiodide

The Use of Ureates as Activators for Samarium Diiodide

Synthesis and Structure Elucidation of 1-Aryl-substituted Tetrahydropyridone Derivatives

Chemistry of Aminimides

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