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

被引：52
作者：
Kshirsagar, Umesh A. [1 ]
Mhaske, Santosh B. [1 ]
Argade, Narshinha P. [1 ]
机构：
[1] Natl Chem Lab, Div Organ Chem Synth, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 18期
关键词：
diamides; HMDS/I-2; intramolecular dehydrative cyclizations; natural and unnatural quinazolinones; synthesis;
D O I：
10.1016/j.tetlet.2007.03.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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收藏
页码：3243 / 3246
页数：4
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