New preparation of benzo-2,1,3-oxadiazoles (benzofurazans)

The synthesis of 1,2,3,4-benzotetrazine 1-oxides (BTOs) is described. Bromo-BTOs 4b−d were prepared by the intramolecular cyclization of diazonium salts bearing an ortho-(tertbutyl)-NNO-azoxy group. BTOs bearing electron-releasing substituents were obtained by nucleophilic displacements of bromine in 4b−d. The formation of the BTO cyclic system involves the intermediate 2-(tert-butyl)-1,2,3,4-benzotetraz-[a] N.

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“…5‐Nitrobenzofurazan (6j): Aniline 1j gave 140 mg (60 %) of 6j as a colorless solid, m.p. 64−66 °C (from CH 2 Cl 2 ) (ref 20. 65−66 °C).…”

Section: Methodsmentioning

confidence: 99%

A New Cyclization Involving the Diazonium and ortho-(tert-Butyl)-NNO-azoxy Groups − Synthesis of 1,2,3,4-Benzotetrazine 1-Oxides

et al. 2002

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“…After that, the benzofurazan compounds having various kinds of substituent groups were synthesized by reduction using hydroxylamine (Gaughran et al, 1954), trialkylphosphite (Boulton et al, 1965;Ghosh and Whitehouse, 1968a) or triphenylphosphine (Boyer and Ellzey 1961;Mallory and Varimbi, 1963;Ceré et al, 1972). The benzofurazan skeleton was also constructed by the cyclization of N-(onitrophenyl)carbamates (Prokipcak et al, 1969;Prokipcak and Forte, 1970) or the cyclization of o-nitrosoazide derivatives (Boulton et al, 1966a).…”

Section: Historymentioning

confidence: 99%

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Uchiyama

Santa

Okiyama

et al. 2001

Biomedical Chromatography

151

101

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Fluorogenic and fluorescent labeling reagents having a benzofurazan (2,1,3-benzoxadiazole) skeleton such as 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), 4-N,N-dimethylaminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (DBD-F), 4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (ABD-F), ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F), 4-hydrazino-7-nitro-2,1,3-benzoxadiazole (NBD-H), 4-N,N-dimethylaminosulfonyl-7-hydrazino-2,1,3-benzoxadiazole (DBD-H), 4-nitro-7-N-piperazino-2,1,3-benzoxadiazole (NBD-PZ), 4-N,N-dimethylaminosulfonyl-7-N-piperazino-2,1,3-benzoxadiazole (DBD-PZ), 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD-COCl) and 7-N,N-dimethylaminosulfonyl-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS) are reviewed in terms of synthetic method, reactivity, fluorescence characteristics, sensitivity and application to analytes.

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Mass spectra of 1,2-alkylenedioxy-substituted and related benzofurazans and benzofuroxans: differentiation between linear and angular isomers

Takakis¹,

Tsantali²,

Haas³

et al. 1999

J. Mass Spectrom.

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New preparation of benzo-2,1,3-oxadiazoles (benzofurazans)

Abstract: A new procedure for the synthesis of substituted benzo-2,1,3-oxadiazoles (benzofurazans) has been established. The method involved the pyrolysis of substituted methyl N-(0-nitropheny1)carbamates. A possible mechanism for the reaction is outlined.

Cited by 18 publications

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A New Cyclization Involving the Diazonium and ortho-(tert-Butyl)-NNO-azoxy Groups − Synthesis of 1,2,3,4-Benzotetrazine 1-Oxides

A New Cyclization Involving the Diazonium and ortho-(tert-Butyl)-NNO-azoxy Groups − Synthesis of 1,2,3,4-Benzotetrazine 1-Oxides

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Mass spectra of 1,2-alkylenedioxy-substituted and related benzofurazans and benzofuroxans: differentiation between linear and angular isomers

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