Notes. A New Synthesis of the Benzothiazole and Benzoxazole Rings

Jenkins, G. I.; Knevel, Adelbert M.; Davis, Charles R.

doi:10.1021/jo01060a625

Cited by 47 publications

(12 citation statements)

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“…An advanced method involves cyclization of a 2-aminophenol with s-triazines, triethyl orthoformate or isonitriles and 2-hydroxybenzonitrile, photochemically to yield benzoxazole (1) [17][18][19][20][21][22].…”

Section: Jyothi and Merugumentioning

confidence: 99%

An Update on the Synthesis of Benzoxazoles

Jyothi

Merugu

2017

Asian J Pharm Clin Res

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Benzoxazoles being structurally similar to bases adenine and guanine interact with biomolecules present in living systems. These compounds possess antimicrobial, central nervous system activities, antihyperglycemic potentiating activity, analgesic, and anti-inflammatory activity. It can also be used as starting material for other bioactive molecules. Modifications in structure and the biological profiles of new generations of benzoxazoles were found to be more potent with enhanced biological activity. Considering all these, we have prepared this review and discussed the synthesis and biological activities of benzoxazoles.

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Section: Jyothi and Merugumentioning

confidence: 99%

An Update on the Synthesis of Benzoxazoles

Jyothi

Merugu

2017

Asian J Pharm Clin Res

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“…The condensation of 2-aminophenol and carboxylic acid 17 or its surrogates such as aldehydes, [18][19][20][21] acid chlorides, [22][23][24] orthoesters, [25][26][27] and β-oxodithioesters 28 under various reaction conditions are the straight forward approaches to construct the benzoxazole unit. However, these methods are often associated with several limitations such as the use of highly toxic reagents, strong acids and, in some cases, harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Aryl Benzoxazoles from Aldoximes

Panda¹

2017

MOJBOC

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Wide spectrum of biological activities of benzoxazole heterocycles aroused great interest for the development of newer methods for their synthesis. We herein report a copper catalyzed method for the synthesis of 2-aryl benzoxazoles from the reaction of aldoxime and 2-iodobromobenzene using N,N'-dimethyl ethylenediamine (DMEDA) as the ligand. The reaction proceeds with the copper-catalyzed dehydration of aldoxime leading to the nitilium ion which might be undergoing hydrolysis and subsequent C-O bond formation in one-pot to afford 2-aryl benzoxazoles. The pure products were isolated and characterized by 1 H NMR, and 13 C NMR data.

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“…These heterocycles shows different pharmacological properties such as antibacterial 6 , antiviral 7 , antifugal 8 , anticancer 9 , anticonvulsant 10 and immunosuppressant 11 . These heterocycles can be prepared by condensing carboxylic acid 12 , acid chloride 13,14 , orthoester [15][16][17] , esters 18 and aldehydes [19][20][21][22][23][24] with o-phenylenediamine, o-aminophenols and o-aminothaiophenols, dehydration of o-acylaminophenols 25 , reaction of o-quinones with amines 26 and Beckmann rearrangement of o-acylphenoloximes 27 . The most common method of synthesis of these heterocycles includes condensation of o-phenylenediamine, o-aminophenol or o-aminothiophenol with suitable aldehyde [28][29][30][31][32] .…”

Section: Introductionmentioning

confidence: 99%