Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones

Xiaobing Wang; Seth Dixon; Mark J. Kurth; Kit Lam

doi:10.1016/j.tetlet.2005.06.012

Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones

Xiaobing Wang, Seth Dixon, Mark J. Kurth, Kit Lam

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

9 Scopus citations

Abstract

A traceless solid-phase route to 1,4-disubstituted-6-nitro-3,4-dihydro-1H- quinazolin-2-ones is described. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl) propionic acid was tethered to Rink resin via its carboxylic group. The protected amine was coupled with an organic acid after Alloc-deprotection and the arylfluorine was displaced with a primary amine to generate a resin-bound aniline with two diversity points. The aniline was released via cleavage to produce the desired products in high yield and purity.

Original language	English (US)
Pages (from-to)	5361-5364
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2005.06.012
State	Published - Aug 8 2005

Keywords

3,4-Dihydro-1H-quinoline-2-one
Solid-phase synthesis
Traceless cleavage

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tetlet.2005.06.012

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title = "Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones",

abstract = "A traceless solid-phase route to 1,4-disubstituted-6-nitro-3,4-dihydro-1H- quinazolin-2-ones is described. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl) propionic acid was tethered to Rink resin via its carboxylic group. The protected amine was coupled with an organic acid after Alloc-deprotection and the arylfluorine was displaced with a primary amine to generate a resin-bound aniline with two diversity points. The aniline was released via cleavage to produce the desired products in high yield and purity.",

keywords = "3,4-Dihydro-1H-quinoline-2-one, Solid-phase synthesis, Traceless cleavage",

author = "Xiaobing Wang and Seth Dixon and Kurth, {Mark J.} and Kit Lam",

year = "2005",

month = aug,

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doi = "10.1016/j.tetlet.2005.06.012",

language = "English (US)",

volume = "46",

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journal = "Tetrahedron Letters",

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T1 - Traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro- 1H-quinoline-2-ones

AU - Wang, Xiaobing

AU - Dixon, Seth

AU - Kurth, Mark J.

AU - Lam, Kit

PY - 2005/8/8

Y1 - 2005/8/8

N2 - A traceless solid-phase route to 1,4-disubstituted-6-nitro-3,4-dihydro-1H- quinazolin-2-ones is described. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl) propionic acid was tethered to Rink resin via its carboxylic group. The protected amine was coupled with an organic acid after Alloc-deprotection and the arylfluorine was displaced with a primary amine to generate a resin-bound aniline with two diversity points. The aniline was released via cleavage to produce the desired products in high yield and purity.

AB - A traceless solid-phase route to 1,4-disubstituted-6-nitro-3,4-dihydro-1H- quinazolin-2-ones is described. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl) propionic acid was tethered to Rink resin via its carboxylic group. The protected amine was coupled with an organic acid after Alloc-deprotection and the arylfluorine was displaced with a primary amine to generate a resin-bound aniline with two diversity points. The aniline was released via cleavage to produce the desired products in high yield and purity.

KW - 3,4-Dihydro-1H-quinoline-2-one

KW - Solid-phase synthesis

KW - Traceless cleavage

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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