Arylboronic Acids. IV. Reactions of Boronophthalide<sup>1</sup>

Lennarz, W. J.; Snyder, H. R.

doi:10.1021/ja01494a021

Cited by 41 publications

(22 citation statements)

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“…The next step was the hydrolysis of the bromide to benzyl alcohol, which underwent intramolecular esterification [8,33,34] The method can be modified by using corresponding benzyl iodide instead of bromide [21] (A1a). 3-Methyl-substituted benzoxaboroles were obtained similarly by using 2-ethylphenylboronic acid [35] (A1b).…”

Section: Methods A: Functionalization Of Boronic Acids and Their Derimentioning

confidence: 99%

Benzoxaboroles – Old compounds with new applications

Adamczyk‐Woźniak

Cyrański

Żubrowska

et al. 2009

Journal of Organometallic Chemistry

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Section: Methods A: Functionalization Of Boronic Acids and Their Derimentioning

confidence: 99%

Benzoxaboroles – Old compounds with new applications

Adamczyk‐Woźniak

Cyrański

Żubrowska

et al. 2009

Journal of Organometallic Chemistry

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“…The 6-aminobenzoboroxole 3 was also functionalized as the corresponding amides 16–20 upon reaction with acetic anhydride 10 , butyric anhydride, trifloroacetic anhydride, succinic anhydride 11 , and phthalic anhydride respectively (Scheme 4). The amide with phthalic anhydride cyclized intramolecularly to provide the cylic imide 20 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of functionalized benzoboroxoles as potential anti-tuberculosis agents

et al. 2016

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Several derivatives of aminobenzoboroxole have been prepared starting from 2-boronobenzaldehyde. All of these derivatives have been evaluated for their anti-mycobacterial activity on Mycobacterium smegmatis and cytotoxicity on breast cancer cell line MCF7. Based on these studies, all the tested molecules have been found to be generally non-toxic and benzoboroxoles with unsubstituted (primary) amines have been found to exhibit good anti-mycobacterial activity. Some of the key compounds have been evaluated for their anti-tubercular activity on Mycobacterium tuberculosis H37Rv using 7H9 and GAST media. 7-Bromo-6-aminobenzoboroxole 4 has been identified as the lead candidate compound for further development.

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“…The reaction of commercially available o-boronobenzaldehyde 1 with sodium borohydride in THF and water provided benzoboroxole 8 in 87% yield. Nitration of benzoboroxole with fuming nitric acid resulted in the formation of 6-nitrobenzoboroxole 9 [8]. Reduction of 9 with Zinc and hydrochloric acid furnished the aminobenzoboroxole 10 in 78% yield (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%