Studien über die Ringschliessung

Meyer, Richard

doi:10.1002/jlac.19033270102

Cited by 18 publications

(5 citation statements)

References 31 publications

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“…Oxalic acid with W-substituted o-phenylenediamines is reported to give only starting material The same product is formed when equimolecular amounts of the two components are used (507). Isosuccinic acid gives the analogous product in poor yield (507): When equimolecular amounts of o-phenylenediamines and dibasic acids are used, it is possible to obtain benzimidazole acids. 0-(2-Benzimidazole)propionic acid may be obtained by heating equimolecular amounts of o-phenylenediamine dihydrochloride, succinic acid, and sodium carbonate to 180°C.…”

Section: B Dibasic Acidsmentioning

confidence: 98%

“…Oxalic acid gives 2,3-dihydroxyquinoxaIines (573,576,666). Oxalic acid with W-substituted o-phenylenediamines is reported to give only starting material The same product is formed when equimolecular amounts of the two components are used (507). Isosuccinic acid gives the analogous product in poor yield (507): When equimolecular amounts of o-phenylenediamines and dibasic acids are used, it is possible to obtain benzimidazole acids.…”

Section: B Dibasic Acidsmentioning

confidence: 99%

“…0-(2-Benzimidazole)propionic acid may be obtained by heating equimolecular amounts of o-phenylenediamine dihydrochloride, succinic acid, and sodium carbonate to 180°C. (507).…”

Section: B Dibasic Acidsmentioning

confidence: 99%

“…Anhydrides of dibasic acids that have been condensed with o-phenylenediamines to give benzimidazole acids of this type are listed in table 5. In several cases amides (11,143,508), or phthalanils (73,509) have been obtained as byproducts.…”

mentioning

confidence: 99%

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The Chemistry of the Benzimidazoles.

Wright¹

1951

Chem. Rev.

436

175

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Section: B Dibasic Acidsmentioning

confidence: 98%

Section: B Dibasic Acidsmentioning

confidence: 99%

“…0-(2-Benzimidazole)propionic acid may be obtained by heating equimolecular amounts of o-phenylenediamine dihydrochloride, succinic acid, and sodium carbonate to 180°C. (507).…”

Section: B Dibasic Acidsmentioning

confidence: 99%

mentioning

confidence: 99%

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The Chemistry of the Benzimidazoles.

Wright¹

1951

Chem. Rev.

436

175

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“…Reduction time: 1 hour. After recrystallization from alcohol, the product melted at 189° ( 34). Yield: 2.5 g. (93.5%).…”

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confidence: 99%

An Improved Method for the Preparation of Fluorine-Substituted Aromatic Amines

Bergmann¹,

Bentov²

1954

J. Org. Chem.

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The usual method for the preparation of fluoro-substituted aromatic amines consists in the diazotization of nitro-substituted aromatic amines, precipitation and decomposition of the diazonium borofluorides (Schiemann reaction), and reduction of the nitro group in the nitrofluoro compounds obtained. However, the decomposition of these diazonium borofluorides is "tempestuous and unorderly, and special methods are required for handling them" (1). In addition, the over-all yields in this reaction are generally unsatisfactory; they range from to 50%. Following occasional observations in the literature (2), the behavior of monoacetyl diamines in the diazotization and the Schiemann reaction was investigated. It was found that the m-and ^-representatives of this series can be diazotized easily, without loss of the acetyl group, and that the Schiemann reaction can be applied to the diazonium compounds formed. Decomposition of the diazonium borofluorides proceeds smoothly and gives the N-acetyl derivatives of the desired fluoroaromatic amines in satisfactory yield. Thus, the following compounds have been prepared (the figures in parenthesis indicate the over-all yield): p-fluoroacetanilide from V-acetyl-p-phenylenediamine (82%); m-fluoroacetanilide from V-acetyl-m-phenylenediamine (75%); 4-fiuoro-4'-acetamidobiphenyl from V-acetylbenzidine (62%); 4-fluoro-4'-acetamido-3,3'-dimethoxybiphenyl from V-acetyl-o-dianisidine (37 %); 4'-fluoro-2-acetamidobiphenyl from 4'-amino-2-acetamidobiphenyl (59%); 4-fluoro-1 -acetamido-

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[1,4]Diazepines with [B]‐Fused Rings

Fryer

Walser

1991

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Studien über die Ringschliessung

Cited by 18 publications

References 31 publications

The Chemistry of the Benzimidazoles.

The Chemistry of the Benzimidazoles.

An Improved Method for the Preparation of Fluorine-Substituted Aromatic Amines

[1,4]Diazepines with [B]‐Fused Rings

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