Synthesis, structure, and antifungal activity of dihydropyridones containing boronate esters
β Scribed by Francis E. Appoh; Susan L. Wheaton; Christopher M. Vogels; Felix J. Baerlocher; Andreas Decken; Stephen A. Westcott
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 252 KB
- Volume
- 20
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20512
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β¦ Synopsis
Abstract
We have prepared a series of novel 2,3βdihydroβ4βpyridones containing boronate esters using the aza DielsβAlder reaction with Danishefsky's diene and imines derived from formylphenylboronic acids. This reaction can be carried out in moderate to high yields using Yb(OTf)~3~ as a Lewis acid catalyst. Two new boron compounds exhibited moderate antifungal activity (at 100 ΞΌg disk^β1^) using Amphotericin B as a control. Β© 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:56β63, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20512
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Sulfonamides containing pinacol pro- tected boronate ester groups have been prepared by the addition of H 2 NC 6 H 4 Bpin (pin = O 2 C 2 Me 4 ) to sulfonyl chlorides p-RC 6 H 4 SO 2 Cl (R = CH 3 , NO 2 ). Hydrogenation of the nitro derivatives afford the corresponding sulfanilamides without compromi