Diazole, Triazole, and Tetrazole N-Oxides

Begtrup, Mikael

doi:10.1016/b978-0-12-396531-8.00001-8

Cited by 28 publications

(12 citation statements)

References 140 publications

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“…Because of regioselective reactivity, many N-oxide derivatives are used in the synthesis of a number of organic compounds [1][2][3][4][5][6][7]. Imidazole N-oxides act as precursors of biologically active molecules, transition metal chelating agents [8,9], and inhibitors of the release of interleukin-1, cytokine release, and protein kinase p38 [10,11]. Some imidazole N-oxide derivatives exhibit anti-inflammatory and antiprotozoal activity [10,12,13].…”

Section: Introductionmentioning

confidence: 99%

Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

et al. 2017

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The crystal structures of new N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives are reported. The results of X-ray diffraction showed the existence of intramolecular hydrogen bonding between carboxamide nitrogen donors and N-oxide oxygen acceptors. The use of Quantum Theory of Atoms in Molecules allowed its classification as a strong interaction, with energy about 10 kcal/mol, and of intermediate character between closed shell and shared bonds. Comparison of experimental data and quantum theoretical calculations indicated that a substituent attached to the phenyl ring in the para position influences the strength and geometry of the title hydrogen bonding. Stronger π-electronwithdrawing properties of the higher energy substituent of the intramolecular hydrogen bond are observed. Among other intermolecular contacts in the studied crystals are C-H…O/ C-H…N hydrogen bonds of imidazole carbon atoms and some π…π stacking interactions between aromatic molecular fragments. Their importance in stabilization of the crystal structure was confirmed by the results of Hirshfeld surface analysis.

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Section: Introductionmentioning

confidence: 99%

Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

et al. 2017

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“…The structure of the products can be explained by dipolar cycloaddition of Noxide to alkene and subsequent ring opening of the isoxazolidine cycloadduct, although different reaction pathways may be in operation, especially considering the presence of Ag salts in the reaction mixture. A similar cycloaddition mechanism is possible for the reaction described earlier by Wu and coworkers, who generated 4-haloisoquinoline N-oxides from 2-alkynylbenzaldoximes upon the action of Br 2 or ICl in the presence of α,β-unsaturated carbonyl compounds, although the authors themselves proposed a different, very complicated mechanism which does not involve an isoxazolidine intermediate [57].…”

Section: Cycloaddition To Carbon-carbon Multiple Bondsmentioning

confidence: 74%

“…Heterocyclic N-oxides are readily available and versatile substrates for preparation of highly functionalized nitrogen heterocycles [1][2][3][4][5]. General and useful synthetic methods exploiting N-oxides as starting materials have been developed, such as cine [6][7][8][9][10][11][12] and other types [13][14][15] of nucleophilic substitution, metalation with organometallic reagents [16], or, more recently, transition metal-catalyzed C-H activation of N-oxides of azines [17][18][19][20][21][22][23][24][25][26][27][28][29] and azoles [30][31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Cycloaddition Reactions of Heterocyclic N-Oxides

Loska

2017

Topics in Heterocyclic Chemistry

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1,3-Dipolar cycloaddition of N-oxides of azines and azoles has become a reliable and versatile synthetic method of preparation of highly functionalized nitrogen heterocycles. Mechanisms of cycloaddition of N-oxides are outlined, including various reaction pathways available for the initial five-membered cycloadducts. Cycloaddition to multiple carbon-carbon, carbon-nitrogen, and carbon-sulfur bonds is discussed, with particular emphasis on modern methods of selective C-2-functionalization of the heteroaromatic ring.

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“…11 Also, 1-hydroxy-imidazoles may be used as insecticides or as plant growth regulators. 12,13 As a result, studies on efficient syntheses of 1-hydroxy-imidazole derivatives have received much attention.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of novel 1-hydroxy-2,4,5-trisubstituted imidazole derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and 1,3-dicarbonyl compounds

Alizadeh-Bami¹,

Salehzadeh²,

Mehrabi³

et al. 2019

Arkivoc

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A simple, and efficient procedure for the synthesis of novel 2,5-diaryl-1-hydroxy-1H-imidazol-4-yl derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and cyclic 1,3dicarbonyl compounds (Melrum's acid or dimedone) in ethanol under reflux conditions without using bases and catalysts is reported. All the products were obtained in good yields and their structures were established from their spectroscopic data.

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Diazole, Triazole, and Tetrazole N-Oxides

Cited by 28 publications

References 140 publications

Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

Recent Advances in Cycloaddition Reactions of Heterocyclic N-Oxides

Efficient synthesis of novel 1-hydroxy-2,4,5-trisubstituted imidazole derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and 1,3-dicarbonyl compounds

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