Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives

Moon Kook Jeon; Dong Su Kim; Ju La Hyun; Deok Chan Ha; Young Dae Gong

doi:10.1016/j.tetlet.2005.09.015

Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives

Moon Kook Jeon, Dong Su Kim, Ju La Hyun, Deok Chan Ha, Young Dae Gong

College of Science

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

14 Citations (Scopus)

Abstract

We were able to obtain 2-cyanoquinazolin-4(3H)-ones 11 in 35-60% four-step overall isolated yields and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-ones 12 in 20-71% four-step overall isolated yields utilizing polymer-bound anthranilic acid derivatives 1, and 6-amino-2-cyanoquinazolin-4(3H)-ones 19 in 30-44% six-step overall isolated yields making use of anthranilic acid derivative resin 2 via dithiazole resins 10 and 17. The reactions on solid phase were monitored by single bead ATR-FTIR spectroscopic method.

Original language	English
Pages (from-to)	7477-7481
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.015
Publication status	Published - 2005 Oct 31

Keywords

Anthranilic acid
Dithiazole
Quinazolinone
Solid-phase synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.09.015

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@article{a6726990af984c66818dc60647de94cb,

title = "Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives",

abstract = "We were able to obtain 2-cyanoquinazolin-4(3H)-ones 11 in 35-60% four-step overall isolated yields and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-ones 12 in 20-71% four-step overall isolated yields utilizing polymer-bound anthranilic acid derivatives 1, and 6-amino-2-cyanoquinazolin-4(3H)-ones 19 in 30-44% six-step overall isolated yields making use of anthranilic acid derivative resin 2 via dithiazole resins 10 and 17. The reactions on solid phase were monitored by single bead ATR-FTIR spectroscopic method.",

keywords = "Anthranilic acid, Dithiazole, Quinazolinone, Solid-phase synthesis",

author = "Jeon, {Moon Kook} and Kim, {Dong Su} and Hyun, {Ju La} and Ha, {Deok Chan} and Gong, {Young Dae}",

note = "Funding Information: We are grateful to Ministry of Commerce, Industry and Energy of Korea, the Center for Biological Modulators, and Korea Research Institute of Chemical Technology, for financial support of this research. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

year = "2005",

month = oct,

day = "31",

doi = "10.1016/j.tetlet.2005.09.015",

language = "English",

volume = "46",

pages = "7477--7481",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "44",

}

TY - JOUR

T1 - Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives

AU - Jeon, Moon Kook

AU - Kim, Dong Su

AU - Hyun, Ju La

AU - Ha, Deok Chan

AU - Gong, Young Dae

N1 - Funding Information: We are grateful to Ministry of Commerce, Industry and Energy of Korea, the Center for Biological Modulators, and Korea Research Institute of Chemical Technology, for financial support of this research. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2005/10/31

Y1 - 2005/10/31

N2 - We were able to obtain 2-cyanoquinazolin-4(3H)-ones 11 in 35-60% four-step overall isolated yields and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-ones 12 in 20-71% four-step overall isolated yields utilizing polymer-bound anthranilic acid derivatives 1, and 6-amino-2-cyanoquinazolin-4(3H)-ones 19 in 30-44% six-step overall isolated yields making use of anthranilic acid derivative resin 2 via dithiazole resins 10 and 17. The reactions on solid phase were monitored by single bead ATR-FTIR spectroscopic method.

AB - We were able to obtain 2-cyanoquinazolin-4(3H)-ones 11 in 35-60% four-step overall isolated yields and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-ones 12 in 20-71% four-step overall isolated yields utilizing polymer-bound anthranilic acid derivatives 1, and 6-amino-2-cyanoquinazolin-4(3H)-ones 19 in 30-44% six-step overall isolated yields making use of anthranilic acid derivative resin 2 via dithiazole resins 10 and 17. The reactions on solid phase were monitored by single bead ATR-FTIR spectroscopic method.

KW - Anthranilic acid

KW - Dithiazole

KW - Quinazolinone

KW - Solid-phase synthesis

UR - http://www.scopus.com/inward/record.url?scp=26244460405&partnerID=8YFLogxK

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U2 - 10.1016/j.tetlet.2005.09.015

DO - 10.1016/j.tetlet.2005.09.015

M3 - Article

AN - SCOPUS:26244460405

SN - 0040-4039

VL - 46

SP - 7477

EP - 7481

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives

Abstract

Keywords

ASJC Scopus subject areas

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