Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl- 4-phenylnicotinates), a new type of 2,2′-azopyridine dyes

Daniel Botelho Da Silva; Abdelouahid Samadi; Lourdes Infantes; María Do Carmo Carreiras; José Marco-Contelles

doi:10.1016/j.tetlet.2010.09.095

Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl- 4-phenylnicotinates), a new type of 2,2′-azopyridine dyes

Daniel Botelho Da Silva, Abdelouahid Samadi, Lourdes Infantes, María Do Carmo Carreiras, José Marco-Contelles

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

8 Citations (Scopus)

Abstract

An unexpected, but simple method for the efficient synthesis of new 2.2′-azopyridine dyes, such as (E)-diethyl 6,6′-(diazene-1,2-diyl) bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, and 11) with NBS/benzoyl peroxide, is described. The X-ray diffraction analysis and the UV-vis absorption spectra of dye 2 are reported and discussed.

Original language	English
Pages (from-to)	6278-6281
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.095
Publication status	Published - Dec 1 2010
Externally published	Yes

Keywords

(E)-Diethyl 6,6′-(diazene-1,2-diyl)bis(5- cyano-2-methyl-4-phenylnicotinates)
2.2′-Azopyridine
Dyes
Ethyl 6-amino-5-cyano-2-methyl-4- arylnicotinates
NBS
Oxidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.09.095

Cite this

@article{4b2b5004fbfb4b85805d1f216234debf,

title = "Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl- 4-phenylnicotinates), a new type of 2,2′-azopyridine dyes",

abstract = "An unexpected, but simple method for the efficient synthesis of new 2.2′-azopyridine dyes, such as (E)-diethyl 6,6′-(diazene-1,2-diyl) bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, and 11) with NBS/benzoyl peroxide, is described. The X-ray diffraction analysis and the UV-vis absorption spectra of dye 2 are reported and discussed.",

keywords = "(E)-Diethyl 6,6′-(diazene-1,2-diyl)bis(5- cyano-2-methyl-4-phenylnicotinates), 2.2′-Azopyridine, Dyes, Ethyl 6-amino-5-cyano-2-methyl-4- arylnicotinates, NBS, Oxidation",

author = "{Da Silva}, {Daniel Botelho} and Abdelouahid Samadi and Lourdes Infantes and Carreiras, {Mar{\'i}a Do Carmo} and Jos{\'e} Marco-Contelles",

note = "Funding Information: Daniel da Silva thanks the Funda{\c c}{\~a}o para a Ci{\^e}ncia e Tecnologia do Minist{\'e}rio da Ci{\^e}ncia, Tecnologia e Ensino Superior of Portugal for his grant belonging to project PTDC/SAU-NEU/64151/2006. A.S. thanks the CSIC for a I3P post-doctoral contract. J.M.C. thanks also the MICINN ( SAF2006-08764-C02-01 ; SAF2009-07271 ), Comunidad de Madrid ( S/SAL-0275-2006 ), and the Instituto de Salud Carlos III [ Retic RENEVAS ( RD06/0026/1002 )] for support. ",

year = "2010",

month = dec,

day = "1",

doi = "10.1016/j.tetlet.2010.09.095",

language = "English",

volume = "51",

pages = "6278--6281",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "48",

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TY - JOUR

T1 - Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl- 4-phenylnicotinates), a new type of 2,2′-azopyridine dyes

AU - Da Silva, Daniel Botelho

AU - Samadi, Abdelouahid

AU - Infantes, Lourdes

AU - Carreiras, María Do Carmo

AU - Marco-Contelles, José

N1 - Funding Information: Daniel da Silva thanks the Fundação para a Ciência e Tecnologia do Ministério da Ciência, Tecnologia e Ensino Superior of Portugal for his grant belonging to project PTDC/SAU-NEU/64151/2006. A.S. thanks the CSIC for a I3P post-doctoral contract. J.M.C. thanks also the MICINN ( SAF2006-08764-C02-01 ; SAF2009-07271 ), Comunidad de Madrid ( S/SAL-0275-2006 ), and the Instituto de Salud Carlos III [ Retic RENEVAS ( RD06/0026/1002 )] for support.

PY - 2010/12/1

Y1 - 2010/12/1

N2 - An unexpected, but simple method for the efficient synthesis of new 2.2′-azopyridine dyes, such as (E)-diethyl 6,6′-(diazene-1,2-diyl) bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, and 11) with NBS/benzoyl peroxide, is described. The X-ray diffraction analysis and the UV-vis absorption spectra of dye 2 are reported and discussed.

AB - An unexpected, but simple method for the efficient synthesis of new 2.2′-azopyridine dyes, such as (E)-diethyl 6,6′-(diazene-1,2-diyl) bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, and 11) with NBS/benzoyl peroxide, is described. The X-ray diffraction analysis and the UV-vis absorption spectra of dye 2 are reported and discussed.

KW - (E)-Diethyl 6,6′-(diazene-1,2-diyl)bis(5- cyano-2-methyl-4-phenylnicotinates)

KW - 2.2′-Azopyridine

KW - Dyes

KW - Ethyl 6-amino-5-cyano-2-methyl-4- arylnicotinates

KW - NBS

KW - Oxidation

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SN - 0040-4039

VL - 51

SP - 6278

EP - 6281

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl- 4-phenylnicotinates), a new type of 2,2′-azopyridine dyes

Abstract

Keywords

ASJC Scopus subject areas

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