Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones |
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Authors: | Umesh A. Kshirsagar |
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Affiliation: | Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India |
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Abstract: | A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (−)-circumdatin-F and (−)-fumiquinazoline-F. |
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Keywords: | Diamides HMDS/I2 Intramolecular dehydrative cyclizations Natural and unnatural quinazolinones Synthesis |
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