A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Alexander Aizikovich; Vladimir Kuznetsov; Sofia Gorohovsky; Amalia Levy; Simha Meir; Gerardo Byk; Garry Gellerman

doi:10.1016/j.tetlet.2004.04.032

A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Alexander Aizikovich
, Vladimir Kuznetsov
, Sofia Gorohovsky
, Amalia Levy
, Simha Meir
, Gerardo Byk
, Garry Gellerman

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

19 Scopus citations

Abstract

Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.

Original language	English
Pages (from-to)	4241-4243
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.032
State	Published - 24 May 2004
Externally published	Yes

Keywords

Azide
DPPA
Pyridin-4-one
Quinazolin-4-ol
Quinolin-4-one

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.04.032

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Aizikovich, A., Kuznetsov, V., Gorohovsky, S., Levy, A., Meir, S., Byk, G., & Gellerman, G. (2004). A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts. Tetrahedron Letters, 45(22), 4241-4243. https://doi.org/10.1016/j.tetlet.2004.04.032

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title = "A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts",

abstract = "Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.",

keywords = "Azide, DPPA, Pyridin-4-one, Quinazolin-4-ol, Quinolin-4-one",

author = "Alexander Aizikovich and Vladimir Kuznetsov and Sofia Gorohovsky and Amalia Levy and Simha Meir and Gerardo Byk and Garry Gellerman",

year = "2004",

month = may,

day = "24",

doi = "10.1016/j.tetlet.2004.04.032",

language = "English",

volume = "45",

pages = "4241--4243",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "22",

}

Aizikovich, A, Kuznetsov, V, Gorohovsky, S, Levy, A, Meir, S, Byk, G & Gellerman, G 2004, 'A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts', Tetrahedron Letters, vol. 45, no. 22, pp. 4241-4243. https://doi.org/10.1016/j.tetlet.2004.04.032

A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts. / Aizikovich, Alexander; Kuznetsov, Vladimir; Gorohovsky, Sofia et al.
In: Tetrahedron Letters, Vol. 45, No. 22, 24.05.2004, p. 4241-4243.

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

TY - JOUR

T1 - A new application of diphenylphosphorylazide (DPPA) reagent

T2 - Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

AU - Aizikovich, Alexander

AU - Kuznetsov, Vladimir

AU - Gorohovsky, Sofia

AU - Levy, Amalia

AU - Meir, Simha

AU - Byk, Gerardo

AU - Gellerman, Garry

PY - 2004/5/24

Y1 - 2004/5/24

N2 - Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.

AB - Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.

KW - Azide

KW - DPPA

KW - Pyridin-4-one

KW - Quinazolin-4-ol

KW - Quinolin-4-one

UR - https://www.scopus.com/pages/publications/2342547062

U2 - 10.1016/j.tetlet.2004.04.032

DO - 10.1016/j.tetlet.2004.04.032

M3 - Article

AN - SCOPUS:2342547062

SN - 0040-4039

VL - 45

SP - 4241

EP - 4243

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 22

ER -

A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Abstract

Keywords

ASJC Scopus subject areas

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