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

Umesh A. Kshirsagar; Santosh B. Mhaske; Narshinha P. Argade

doi:10.1016/j.tetlet.2007.03.032

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

Umesh A. Kshirsagar, Santosh B. Mhaske, Narshinha P. Argade

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

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.

Original language	English
Pages (from-to)	3243-3246
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2007.03.032
State	Published - 30 Apr 2007
Externally published	Yes

Keywords

Diamides
HMDS/I
Intramolecular dehydrative cyclizations
Natural and unnatural quinazolinones
Synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.03.032

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

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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AU - Kshirsagar, Umesh A.

AU - Mhaske, Santosh B.

AU - Argade, Narshinha P.

PY - 2007/4/30

Y1 - 2007/4/30

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AB - 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.

KW - Diamides

KW - HMDS/I

KW - Intramolecular dehydrative cyclizations

KW - Natural and unnatural quinazolinones

KW - Synthesis

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SN - 0040-4039

VL - 48

SP - 3243

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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