Isatoic Anhydrides and Their Uses in Heterocyclic Synthesis

Kappe, Thomas; Stadlbauer, W.

doi:10.1016/s0065-2725(08)60042-2

Cited by 44 publications

(25 citation statements)

References 170 publications

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“…Recently, IA derivatives, mainly N -methyl-IA and 1-methyl-7-nitro-IA, were also used to alter the ribose moiety of tRNA and mRNA for further structural and functional studies3536. Three types of reactions have been commonly used to prepare IA: (1) cyclization of anthranilic acid with carbonic acid derivatives, (2) oxidation of isatin in glacial acetic acid and (3) rearrangement of phthalic acid derivatives (SI Scheme S1)37.…”

Section: Resultsmentioning

confidence: 99%

An Exceptionally Facile Two-Step Structural Isomerization and Detoxication via a Water-Assisted Double Lossen Rearrangement

Huang

Xie

et al. 2016

Sci Rep

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N-hydroxyphthalimide (NHPI), which is best known as an organocatalyst for efficient C-H activation, has been found to be oxidized by quinoid compounds to its corresponding catalytically active nitroxide-radical. Here, we found that NHPI can be isomerized into isatoic anhydride by an unusually facile two-step method using tetrachloro-1,4-benzoquinone (TCBQ, p-chloranil), accompanied by a two-step hydrolytic dechlorination of highly toxic TCBQ into the much less toxic dihydroxylation product, 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid). Interestingly, through the complementary application of oxygen-18 isotope-labeling, HPLC combined with electrospray ionization quadrupole time-of-flight and high resolution Fourier transform ion cyclotron resonance mass spectrometric studies, we determined that water was the source and origin of oxygen for isatoic anhydride. Based on these data, we proposed that nucleophilic attack with a subsequent water-assisted Lossen rearrangement coupled with rapid intramolecular addition and cyclization in two consecutive steps was responsible for this unusual structural isomerization of NHPI and concurrent hydroxylation/detoxication of TCBQ. This is the first report of an exceptionally facile double-isomerization of NHPI via an unprecedented water-assisted double-Lossen rearrangement under normal physiological conditions. Our findings may have broad implications for future research on hydroxamic acids and polyhalogenated quinoid carcinogens, two important classes of compounds of major chemical and biological interest.

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Section: Resultsmentioning

confidence: 99%

An Exceptionally Facile Two-Step Structural Isomerization and Detoxication via a Water-Assisted Double Lossen Rearrangement

Huang

Xie

et al. 2016

Sci Rep

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“…3,1-Benzoxazine-2,4-diones (isatoic anhydrides) are versatile heterocyclic intermediates used in the synthesis of a wide range of heterocyclic scaffolds [11][12][13]. Based on the literature reports [14][15][16][17], the condensation of 1,2-phenylenediamines 1 with 3,1-benzoxazine-2,4-diones 2 could lead to the formation of substituted benzimidazole derivatives, featuring 2-(1H-benzo[d]imidazol-2-yl) benzenamines 3 as the main products, which are accompanied by various amounts of 6,7-dihydrobenzimidazo [l,2-c]quinazolin-6-ones 4 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…The first report [14] described the formation of 8-(2-aminophenyl)theophiline (9) and 1,3-dimethyl-11H-pyrido [4,5-b] [1,4]benzodiazepine-2,4,6(1H,3H,5H)-trione (10) with 22% and 17% yield, respectively. Furthermore, further investigation of the reaction [19] revealed formation of two additional products: 2,6-dimethylpurino [7,8-c]quinazoline-3,5,6(2H,4H,7H)-trione (11) (12% yield) and small amounts of tricycloquinazoline (12). …”

Section: Introductionmentioning

confidence: 99%

N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imid-azol-2-yl)benzeneamine

Dziełak

Trzybiński

Czerwińska

et al. 2018

Molbank

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N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzeneamine was obtained by condensation of N-(4-bromobenzyl)-3,1-benzoxazine-2,4-dione (N-(4-bromobenzyl)isatoic anhydride) with 4,5-dimethyl-1,2-phenylenediamine in refluxing acetic acid. This is a rare example of condensation of N-substituted 3,1-benzoxazine-2,4-dione with 1,2-phenylenediamine, which resulted in the formation of a benzimidazole derivative with a moderate yield. Crystallographic studies and initial biological screening were performed for the obtained product.

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“…In order to form six-membered rings the substrates have to be 1,3-dinucleophiles. These can be N,N'-disubstituted amidines, leading to mesomeric pyrimidine betaines, N-substituted amides leading to 1,3-oxazine betaines, Nsubstituted thioamides leading to 1,3-thiazine betaines, or 1,2,3-triazenes yielding 1,2,3-triazines [7][8][9]. The chemistry of these compounds has been extensively reviewed twenty years ago [8,9].…”

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confidence: 99%

“…These can be N,N'-disubstituted amidines, leading to mesomeric pyrimidine betaines, N-substituted amides leading to 1,3-oxazine betaines, Nsubstituted thioamides leading to 1,3-thiazine betaines, or 1,2,3-triazenes yielding 1,2,3-triazines [7][8][9]. The chemistry of these compounds has been extensively reviewed twenty years ago [8,9]. New results in this area have been mainly concerned with the syntheses of compounds with new medicinal and biological activities [10], or as building blocks (in combination with nitronyl nitroxide radicals) for their use in material sciences [11].…”

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confidence: 99%