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.

引用

页码：3243 / 3246

页数：4

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