Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

TitleHexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
Publication TypeJournal Article
Year of Publication2007
AuthorsKshirsagar, UA, Mhaske, SB, Argade, NP
JournalTetrahedron Letters
Volume48
Issue18
Pagination3243-3246
Date PublishedAPR
Type of ArticleArticle
ISSN0040-4039
Keywordsdiamides, 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.

DOI10.1016/j.tetlet.2007.03.032
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.347

Divison category: 
Organic Chemistry