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

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2269-2272
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	12
DOIs	https://doi.org/10.1039/p19890002269
Publication status	Published - 1989
Externally published	Yes

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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 = "Chemical Society",

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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

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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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