Synthesis of nitrogen-containing heterocyclic compounds by photooxidation of aromatic azides

Chainikova, E. M.; Safiullin, R. L.; Спирихин, Л. В.; Erastov, A. S.

doi:10.1016/j.tetlet.2013.02.036

Cited by 13 publications

(11 citation statements)

References 15 publications

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“…The photolytic source wavelength range was chosen in such a way to minimize the possible photochemical reactions of nitroso oxides. On photooxidation of azide 57, the only product that was isolated and identified was (3,4-dimethyl-3a,4-dihydro-2,1-benzisoxazol-5(3H)-ylidene)acetaldehyde (60) (70% yield) (equation 13) 72,115 . Benzisoxazole 60 is produced via the intramolecular [3 + 2]-cycloaddition of the nitrile oxide group to the double bond in compound 59, which is the product of the corresponding nitroso oxide unimolecular transformations analogous to those shown in Scheme 15.…”

Section: B Products Of Thermal Transformation Of Nitroso Oxides In Smentioning

confidence: 99%

“…Benzisoxazole 60 is produced via the intramolecular [3 + 2]-cycloaddition of the nitrile oxide group to the double bond in compound 59, which is the product of the corresponding nitroso oxide unimolecular transformations analogous to those shown in Scheme 15. To elucidate the effect of the irradiation wavelength range of the photolytic source on the yield of the azide 58 photooxidation products, a quantitative analysis of reaction mixtures using HPLC without isolation of the products was performed (Table 13) 115 . The data in Table 5 show that narrowing the wavelength range decreased the yield of 6-nitroquinoline (63) …”

Section: B Products Of Thermal Transformation Of Nitroso Oxides In Smentioning

confidence: 99%

“…Thus, using the example of five aromatic azides (42a, 42b 113 , 53 73 , 57 72,115 , and 58 115 ), it was demonstrated that during their photooxidation the thermal isomerization reaction of the intermediate nitroso oxides leads to the formation of nitrile oxides. Nitrile oxides with a favorable structure via intramolecular cycloaddition give stable heterocycles.…”

Section: B Products Of Thermal Transformation Of Nitroso Oxides In Smentioning

confidence: 99%

“…With regard to several arylnitroso oxides, it was shown that the consumption of nitroso oxides in the dark leads to the opening of the aromatic ring to form nitrile oxide (Scheme 15, equations 13 and 14) 72,73,115 . The trans-isomers are transformed to the cis-isomers, which are isomerized to nitrile oxides via a two-stage reaction.…”

Section: Some Conclusion About the Mechanism Of Reaction Of The Nitrmentioning

confidence: 99%

“…Imine was determined within the reaction products, which allows the suggestion that the reaction proceeds in accordance with equation 16 107,120 72,73,113,115 , seems to be more probable. In addition, the breaking of the O-O bond in dioxazoline 91 should lead to the formation of stable products-nitrone and ketone (aldehyde), which makes this reaction thermodynamically more favorable.…”

Section: E Reactions Of Nitroso Oxides With Organic Compoundsmentioning

confidence: 99%

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The chemistry of nitroso oxides

Chainikova

Khursan

Safiullin

2014

Patai's Chemistry of Functional Groups

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Nitroso oxides (RNOO) are the isoelectronic analogs of carbonyl oxides (R 2 COO) and ozone (O 3 ) and, as well as these species, possess a three‐centered 4π‐electron system, which determines their chemical properties and reactivity unusual for a family of peroxides. The review is focused on the chemistry of the parent nitroso oxide (HNOO) and its aromatic analogs (ArNOO). The structure, spectral properties, methods for generation, reactivity and mechanisms of various transformations of these species both in the gas and condensed media are discussed in detail. An aromatic substituent significantly stabilizes the π‐system of nitroso oxide. The typical reactions of nitroso oxides are O‐transfer to an appropriate substrate or [3+2]‐cycloaddition to unsaturated bonds. Special attention was paid to the redox isomerization of arylnitroso oxides with ring cleavage that leads to the formation of diene nitrile oxides.

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Section: B Products Of Thermal Transformation Of Nitroso Oxides In Smentioning

confidence: 99%

Section: B Products Of Thermal Transformation Of Nitroso Oxides In Smentioning

confidence: 99%

Section: B Products Of Thermal Transformation Of Nitroso Oxides In Smentioning

confidence: 99%

Section: Some Conclusion About the Mechanism Of Reaction Of The Nitrmentioning

confidence: 99%

Section: E Reactions Of Nitroso Oxides With Organic Compoundsmentioning

confidence: 99%

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The chemistry of nitroso oxides

Chainikova

Khursan

Safiullin

2014

Patai's Chemistry of Functional Groups

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A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

2019

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Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a Brønsted acid HBF4·OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron‐donating and electron‐withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well‐tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.

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The Effects of Molecular Properties on Ready Biodegradation of Aromatic Compounds in the OECD 301B CO2 Evolution Test

Chengfang

Sun

et al. 2015

Arch Environ Contam Toxicol

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Ready biodegradation is the primary biodegradability of a compound, which is used for discriminating whether a compound could be rapidly and readily biodegraded in the natural ecosystems in a short period and has been applied extensively in the environmental risk assessment of many chemicals. In this study, the effects of 24 molecular properties (including 2 physicochemical parameters, 10 geometrical parameters, 6 topological parameters, and 6 electronic parameters) on the ready biodegradation of 24 kinds of synthetic aromatic compounds were investigated using the OECD 301B CO2 Evolution test. The relationship between molecular properties and ready biodegradation of these aromatic compounds varied with molecular properties. A significant inverse correlation was found for the topological parameter TD, five geometrical parameters (Rad, CAA, CMA, CSEV, and N c), and the physicochemical parameter K ow, and a positive correlation for two topological parameters TC and TVC, whereas no significant correlation was observed for any of the electronic parameters. Based on the correlations between molecular properties and ready biodegradation of these aromatic compounds, the importance of molecular properties was demonstrated as follows: geometrical properties > topological properties > physicochemical properties > electronic properties. Our study first demonstrated the effects of molecular properties on ready biodegradation by a number of experiment data under the same experimental conditions, which should be taken into account to better guide the ready biodegradation tests and understand the mechanisms of the ready biodegradation of aromatic compounds.

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Synthesis of nitrogen-containing heterocyclic compounds by photooxidation of aromatic azides

Cited by 13 publications

References 15 publications

The chemistry of nitroso oxides

The chemistry of nitroso oxides

A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

The Effects of Molecular Properties on Ready Biodegradation of Aromatic Compounds in the OECD 301B CO2 Evolution Test

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