Synthesis and characterisation of a new polycyclic phenazine from 1,4-naphthoquinone

Matuzalem J. da Silva; Maria do Carmo F. R. Pinto; Carlos A. de Simone; Janaina G. Soares; Jose R. Machado Reys; Jose D. de Souza Filho; William T. A. Harrison; Carlos E. M. Carvalho; Marilia O. F. Goulart; Eufranio N. da Silva Junior; Antonio V. Pinto

doi:10.1016/j.tetlet.2011.03.006

Synthesis and characterisation of a new polycyclic phenazine from 1,4-naphthoquinone

Matuzalem J. da Silva, Maria do Carmo F. R. Pinto, Carlos A. de Simone, Janaina G. Soares, Jose R. Machado Reys, Jose D. de Souza Filho, William T. A. Harrison, Carlos E. M. Carvalho, Marilia O. F. Goulart, Eufranio N. da Silva Junior, Antonio V. Pinto

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

6 Citations (Scopus)

Abstract

Bioactive naphthoquinone-derived heterocyclic compounds have been prepared. Herein, we describe the semisynthesis of a new phenazine, through modified Hooker's reaction, using lapachol as a precursor. This compound was characterised by 2D NMR spectroscopy methods and X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2415-2418
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	18
Early online date	8 Mar 2011
DOIs	https://doi.org/10.1016/j.tetlet.2011.03.006
Publication status	Published - 4 May 2011

Keywords

lapachol
heterocycles
naphthoquinones
phenazines
nor-beta-lapachone
catalyzed intramolecular hydroamination
trypanosoma-cruzi
intermolecular hydroamination
carboxylic-acids
derivatives
identification
oxoisoaporphine
1,2,3-Triazoles

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10.1016/j.tetlet.2011.03.006

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da Silva, M. J., Pinto, M. D. C. F. R., de Simone, C. A., Soares, J. G., Machado Reys, J. R., de Souza Filho, J. D., Harrison, W. T. A., Carvalho, C. E. M., Goulart, M. O. F., da Silva Junior, E. N., & Pinto, A. V. (2011). Synthesis and characterisation of a new polycyclic phenazine from 1,4-naphthoquinone. Tetrahedron Letters, 52(18), 2415-2418. https://doi.org/10.1016/j.tetlet.2011.03.006

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title = "Synthesis and characterisation of a new polycyclic phenazine from 1,4-naphthoquinone",

abstract = "Bioactive naphthoquinone-derived heterocyclic compounds have been prepared. Herein, we describe the semisynthesis of a new phenazine, through modified Hooker's reaction, using lapachol as a precursor. This compound was characterised by 2D NMR spectroscopy methods and X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.",

keywords = "lapachol, heterocycles, naphthoquinones, phenazines, nor-beta-lapachone, catalyzed intramolecular hydroamination, trypanosoma-cruzi, intermolecular hydroamination, carboxylic-acids, derivatives, identification, oxoisoaporphine, 1,2,3-Triazoles",

author = "{da Silva}, {Matuzalem J.} and Pinto, {Maria do Carmo F. R.} and {de Simone}, {Carlos A.} and Soares, {Janaina G.} and {Machado Reys}, {Jose R.} and {de Souza Filho}, {Jose D.} and Harrison, {William T. A.} and Carvalho, {Carlos E. M.} and Goulart, {Marilia O. F.} and {da Silva Junior}, {Eufranio N.} and Pinto, {Antonio V.}",

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doi = "10.1016/j.tetlet.2011.03.006",

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T1 - Synthesis and characterisation of a new polycyclic phenazine from 1,4-naphthoquinone

AU - da Silva, Matuzalem J.

AU - Pinto, Maria do Carmo F. R.

AU - de Simone, Carlos A.

AU - Soares, Janaina G.

AU - Machado Reys, Jose R.

AU - de Souza Filho, Jose D.

AU - Harrison, William T. A.

AU - Carvalho, Carlos E. M.

AU - Goulart, Marilia O. F.

AU - da Silva Junior, Eufranio N.

AU - Pinto, Antonio V.

PY - 2011/5/4

Y1 - 2011/5/4

N2 - Bioactive naphthoquinone-derived heterocyclic compounds have been prepared. Herein, we describe the semisynthesis of a new phenazine, through modified Hooker's reaction, using lapachol as a precursor. This compound was characterised by 2D NMR spectroscopy methods and X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

AB - Bioactive naphthoquinone-derived heterocyclic compounds have been prepared. Herein, we describe the semisynthesis of a new phenazine, through modified Hooker's reaction, using lapachol as a precursor. This compound was characterised by 2D NMR spectroscopy methods and X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

KW - lapachol

KW - heterocycles

KW - naphthoquinones

KW - phenazines

KW - nor-beta-lapachone

KW - catalyzed intramolecular hydroamination

KW - trypanosoma-cruzi

KW - intermolecular hydroamination

KW - carboxylic-acids

KW - derivatives

KW - identification

KW - oxoisoaporphine

KW - 1,2,3-Triazoles

U2 - 10.1016/j.tetlet.2011.03.006

DO - 10.1016/j.tetlet.2011.03.006

M3 - Article

SN - 0040-4039

VL - 52

SP - 2415

EP - 2418

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Synthesis and characterisation of a new polycyclic phenazine from 1,4-naphthoquinone

Abstract

Keywords

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