Reductive cyclization of carbohydrate 2‐nitrophenylhydrazones to chiral functionalized 1,2,4‐benzotriazines and benzimidazoles

Andersch, Jens; Sicker, Dieter

doi:10.1002/jhet.5570360302

Cited by 14 publications

(2 citation statements)

References 17 publications

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“…A fermentation broth of either 2-OGcA or crystalline 2-OGcMe can be used as a precursor for the preparation of functionalized 1,2,4-benzotriazines and benzimidazoles according to Andersch and Sicker [2] (Fig. 9).…”

Section: -Oxo-d-gluconic Acidmentioning

confidence: 99%

White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical syntheses

Stottmeister

Aurich

Wilde

et al. 2005

J IND MICROBIOL BIOTECHNOL

103

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Functionalized compounds, which are difficult to produce by classical chemical synthesis, are of special interest as biotechnologically available targets. They represent useful building blocks for subsequent organic syntheses, wherein they can undergo stereoselective or regioselective reactions. "White Biotechnology" (as defined by the European Chemical Industry [ http://www.europabio.org/white_biotech.htm ], as part of a sustainable "Green Chemistry,") supports new applications of chemicals produced via biotechnology. Environmental aspects of this interdisciplinary combination include: Use of renewable feedstock Optimization of biotechnological processes by means of: New "high performance" microorganisms On-line measurement of substrates and products in bioreactors Alternative product isolation, resulting in higher yields, and lower energy demand In this overview we describe biotechnologically produced pyruvic, 2-oxopentaric and 2-oxohexaric acids as promising new building blocks for synthetic chemistry. In the first part, the microbial formation of 2-oxocarboxylic acids (2-OCAs) in general, and optimization of the fermentation steps required to form pyruvic acid, 2-oxoglutaric acid, and 2-oxo-D-gluconic acid are described, highlighting the fundamental advantages in comparison to chemical syntheses. In the second part, a set of chemical formula schemes demonstrate that 2-OCAs are applicable as building blocks in the chemical synthesis of, e.g., hydrophilic triazines, spiro-connected heterocycles, benzotriazines, and pyranoic amino acids. Finally, some perspectives are discussed.

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Section: -Oxo-d-gluconic Acidmentioning

confidence: 99%

White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical syntheses

Stottmeister

Aurich

Wilde

et al. 2005

J IND MICROBIOL BIOTECHNOL

103

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“…In contrast, compound (45) formed the benzoimidazole (47) under acid catalysis (Scheme 5). 47 Imidazolin-2-ones (49) was efficiently synthesized by ring contraction of 1,2,4-benzotriazin-3-ones (48) upon treatment with hydroxylamine-O-sulfonic acid in aqueous alkali upon heating. Furthermore, dihydro-1,2,4-benzotriazine (50) was electrochemically reduced with an excess of sodium dithionite in formic acid at pH 4 to benzimidazole (51) (Scheme 6).…”

Section: Scheme 5 Reductive Cyclization Of 2-nitrophenylhydrazone (44)mentioning

confidence: 99%

The synthesis of 1,2,4-benzotriazines

Ziarani¹,

Mostofi²,

Gholamzadeh³

et al. 2019

Arkivoc

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The 1,2,4-benzotriazine nucleus fused to a benzene ring is a prominent heterocyclic substructure present in numerous pharmacologically active compounds. To date, many 1,2,4-benzotriazine analogues possessing a wide spectrum of potent pharmacological activities are known. This review compiles information on the synthesis, chemical reactions, medicinal chemistry aspects and applications of 1,2,4-benzotriazines.

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ChemInform Abstract: Reductive Cyclization of Carbohydrate 2‐Nitrophenylhydrazones to Chiral Functionalized 1,2,4‐Benzotriazines and Benzimidazoles.

Andersch

Sicker

1999

ChemInform

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Reductive cyclization of carbohydrate 2‐nitrophenylhydrazones to chiral functionalized 1,2,4‐benzotriazines and benzimidazoles

Cited by 14 publications

References 17 publications

White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical syntheses

White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical syntheses

The synthesis of 1,2,4-benzotriazines

ChemInform Abstract: Reductive Cyclization of Carbohydrate 2‐Nitrophenylhydrazones to Chiral Functionalized 1,2,4‐Benzotriazines and Benzimidazoles.

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