Synthesis of 4-dimethoxymethyl-6-hydroxy-2-methoxynicotinonitrile: A suggested mechanism revision

Pedro Victory; Julián Sempere; José I. Borrell; Ana Crespo

doi:10.1039/p19890002269

Synthesis of 4-dimethoxymethyl-6-hydroxy-2-methoxynicotinonitrile: A suggested mechanism revision

Pedro Victory^*
, Julián Sempere
, José I. Borrell
, Ana Crespo

^*Autor corresponent d’aquest treball

Producció científica: Article en revista indexada › Article › Avaluat per experts

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Resum

Methyl 4,4-dimethoxy-3-oxobutyrate (1) condenses with malonodinitrile (2) in methanolic sodium methoxide to form 4-dimethoxymethyl-2-methoxypyridine-3- carbonitrile (3a). A previously proposed interpretation of this reaction is shown to be only one of several which allow the formation of one isomer or another [6-alkoxy-2-hydroxy- (4) or 2-alkoxy-6-hydroxy-3-cyano-pyridines] depending on the pH of the medium.

Idioma original	Anglès
Pàgines (de-a)	2269-2272
Nombre de pàgines	4
Revista	Journal of the Chemical Society, Perkin Transactions 1
Número	12
DOIs	https://doi.org/10.1039/p19890002269
Estat de la publicació	Publicada - 1989
Publicat externament	Sí

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title = "Synthesis of 4-dimethoxymethyl-6-hydroxy-2-methoxynicotinonitrile: A suggested mechanism revision",

abstract = "Methyl 4,4-dimethoxy-3-oxobutyrate (1) condenses with malonodinitrile (2) in methanolic sodium methoxide to form 4-dimethoxymethyl-2-methoxypyridine-3- carbonitrile (3a). A previously proposed interpretation of this reaction is shown to be only one of several which allow the formation of one isomer or another [6-alkoxy-2-hydroxy- (4) or 2-alkoxy-6-hydroxy-3-cyano-pyridines] depending on the pH of the medium.",

author = "Pedro Victory and Juli{\'a}n Sempere and Borrell, \{Jos{\'e} I.\} and Ana Crespo",

year = "1989",

doi = "10.1039/p19890002269",

language = "English",

pages = "2269--2272",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Royal Society of Chemistry",

number = "12",

}

TY - JOUR

T1 - Synthesis of 4-dimethoxymethyl-6-hydroxy-2-methoxynicotinonitrile

T2 - A suggested mechanism revision

AU - Victory, Pedro

AU - Sempere, Julián

AU - Borrell, José I.

AU - Crespo, Ana

PY - 1989

Y1 - 1989

N2 - Methyl 4,4-dimethoxy-3-oxobutyrate (1) condenses with malonodinitrile (2) in methanolic sodium methoxide to form 4-dimethoxymethyl-2-methoxypyridine-3- carbonitrile (3a). A previously proposed interpretation of this reaction is shown to be only one of several which allow the formation of one isomer or another [6-alkoxy-2-hydroxy- (4) or 2-alkoxy-6-hydroxy-3-cyano-pyridines] depending on the pH of the medium.

AB - Methyl 4,4-dimethoxy-3-oxobutyrate (1) condenses with malonodinitrile (2) in methanolic sodium methoxide to form 4-dimethoxymethyl-2-methoxypyridine-3- carbonitrile (3a). A previously proposed interpretation of this reaction is shown to be only one of several which allow the formation of one isomer or another [6-alkoxy-2-hydroxy- (4) or 2-alkoxy-6-hydroxy-3-cyano-pyridines] depending on the pH of the medium.

UR - https://www.scopus.com/pages/publications/0041292867

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:A1989CG30600015&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1039/p19890002269

DO - 10.1039/p19890002269

M3 - Article

AN - SCOPUS:0041292867

SN - 1472-7781

SP - 2269

EP - 2272

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 12

ER -

Synthesis of 4-dimethoxymethyl-6-hydroxy-2-methoxynicotinonitrile: A suggested mechanism revision

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