Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
| Title | Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones |
| Publication Type | Journal Article |
| Year of Publication | 2007 |
| Authors | Kshirsagar, UA, Mhaske, SB, Argade, NP |
| Journal | Tetrahedron Letters |
| Volume | 48 |
| Issue | 18 |
| Pagination | 3243-3246 |
| Date Published | APR |
| Type of Article | Article |
| ISSN | 0040-4039 |
| Keywords | diamides, HMDS/I-2, intramolecular dehydrative cyclizations, natural and unnatural quinazolinones, synthesis |
| Abstract | A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 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. (c) 2007 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2007.03.032 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.347 |
Divison category:
Organic Chemistry