Entwicklungen in der Arylnitren‐Chemie: Synthesen und Mechanismen

Iddon, B.; Meth‐Cohn, Otto; Scriven, E. F. V.; Suschitzky, H.; Gallagher, P. T.

doi:10.1002/ange.19790911205

Cited by 52 publications

(4 citation statements)

References 72 publications

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“…A monocyclic aryl nitrene isomerizes to a dehydroazepine intermediate, whereas a polycyclic aryl nitrene preferentially isomerizes to an azirine . The isomeric intermediates, dehydroazepines or azirines, may react with nucleophilic species such as amines, alcohols, thiols, halide ions, or water to give insertion products, 2-substituted 3 H -azepines or 2-substituted anilines, respectively. , The primary product for a triplet aryl nitrene, however, would lead to an aniline generated by sequential hydrogen abstractions from the solvent molecules. The addition products formed in the photolysis of 5-azido-8-methoxypsoralen are from the nitrene intermediate directly.…”

Section: Resultsmentioning

confidence: 99%

Photochemical Reactions of 5-Azido-8-methoxypsoralen

Feng

1996

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Photochemical Reactions of 5-Azido-8-methoxypsoralen

Feng

1996

J. Org. Chem.

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“…It is therefore possible that triplet nitrene photoproducts of 1 and 2 are responsible for their DNA photonicking activity. Hydrogen abstraction is a major pathway for triplet nitrene reaction [36].…”

Section: Discussionmentioning

confidence: 99%

Photocleavage of DNA and photofootprinting of E.coli RNA polymerase bound to promoter DNA by azido-9-acridinylamines

Jeppesen¹,

Buchardt

Henriksen

et al. 1988

Nucleic Acids Research

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The long-wavelength ultraviolet (lambda approximately 420 nm) radiation induced reaction between 6-azido-2-methoxy-9-acridinylamines and supercoiled plasmid DNA results in single strand scissions and formation of covalent adducts (ratio approximately 1:10). By treating azidoacridine-photomodified DNA with piperidine at 90 degrees C, additional strand scissions are observed in a complex sequence dependent manner with an overall preference for T greater than or equal to G greater than C much greater than A. The resulting DNA fragments migrate as 5'-phosphates in polyacrylamide gels. Photofootprinting of the binding site of RNA-polymerase on promoter DNA is demonstrated with an azido-9-acridinylamino-octamethylene-9-aminoacridine. Similar experiments using 9-amino-6-azido-2-methoxyacridine indicate that this reagent recognizes changes in the DNA conformation induced by RNA polymerase binding, in relation to open complex formation.

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“…204-207°C (27%) was clearly not analogous to any of the products isolated from the similar oxidation of (1). Although a molecular equivalent of methanol had again been incorporated into the product and a CH-CH-NH system was apparently still present [as in (10); (Scheme l)], (6 5.64 (d, J 2.8 Hz NH), 5.46 (d, J 5.8 Hz), and 4.01 (ddd, J 5.8, 2.8 and 1.4 Hz, NHCH), the chemical shift and coupling constant of the signal at 6 5.46 was in better agreement with its assignment as an olefinic proton. Assignment of the conjugated diene structure (11) to this product rather than the non-conjugated diene (12) comes from the U.V.…”

Section: T Amentioning

confidence: 99%

Intramolecular reactions of N-nitrenes: oxidation of 3-amino-2-(2,4-dimethoxyphenylbutyl)quinazolin-4(3H)-ones

Atkinson¹

1985

J. Chem. Soc., Perkin Trans. 1

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The N-nitrenes generated by oxidation of N-aminoquinazolones (1) and ( 2) are trapped by the remote 2,4-dimethoxyphenyl ring. Oxidation of (1 ) in benzene gives the metacyclophane (3) in 60% isolated yield whereas oxidation in methanol gives (5), (6) and ( 8). The structures of the acetal (5) and the imine (8) have been confirmed by X-ray crystallography. Oxidation of (2) in methanol yields ( 11) and ( 16). An explanation is offered for the selectivity for attack on the 2,3or 5,6-double bonds of the dimethoxyphenyl ring by the N-nitrene derived from (1).Oxidation of N-aminoquinazolones generates the corresponding N-nitrenes which have been trapped intermolecularly by a variety of functional groups including double bonds and aromatic rings.' We have shown previously that an appropriately substituted and positioned aryl group in a sidechain at position 2 can trap this N-nitrene intramolecularly.* Three different types of reaction with methoxylated phenyl rings which the N-nitrene undergoes are exemplified in Scheme

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Entwicklungen in der Arylnitren‐Chemie: Synthesen und Mechanismen

Abstract: Aryl-und Heteroarylnitrene konnen in ihren beiden

Cited by 52 publications

References 72 publications

Photochemical Reactions of 5-Azido-8-methoxypsoralen

Photochemical Reactions of 5-Azido-8-methoxypsoralen

Photocleavage of DNA and photofootprinting of E.coli RNA polymerase bound to promoter DNA by azido-9-acridinylamines

Intramolecular reactions of N-nitrenes: oxidation of 3-amino-2-(2,4-dimethoxyphenylbutyl)quinazolin-4(3H)-ones

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