e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

2-Cyanopyridazin-3 (2H)-ones: effective and chemoselective electrophilic cyanating agents

JJ Kim, DH Kweon, SD Cho, HK Kim, EY Jung, SG Lee…

Index: Kim, Jeum-Jong; Kweon, Deok-Heon; Cho, Su-Dong; Kim, Ho-Kyun; Jung, Eun-Young; Lee, Sang-Gyeong; Falck; Yoon, Yong-Jin Tetrahedron, 2005 , vol. 61, # 24 p. 5889 - 5894

Full Text: HTML

Citation Number: 31

Abstract

The introduction of a cyano group via carbon–carbon, carbon–nitrogen and carbon–sulfur forming reactions is a fundamental process in organic synthesis. Compounds containing the N-, S-, or C-cyano functional group are also found among many pharmaceuticals and their intermediates. 1 and 2 There are a limited number of reagents that can serve as a cyano cation (CN + ) equivalent or synthon, inter alia, tosyl cyanide, 3 and 4 ...

Benzylamine Structure

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~84%

benzylcyanamide Structure

benzylcyanamide

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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Benzylamine Structure

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~83%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

benzylcyanamide Structure

benzylcyanamide

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2-Acetyltetralone Structure

2-Acetyltetralone

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile Structure

1-oxo-1,2,3,4-t...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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4-Mercaptophenol Structure

4-Mercaptophenol

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

p-Thiocyanatophenol, p-thiocyanato Structure

p-Thiocyanatoph...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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4-Aminophenol Structure

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

N/A Structure

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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4-Aminothiophenol Structure

4-Aminothiophenol

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

4-amino phenyl thiocyanate Structure

4-amino phenyl ...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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Cyclohexylamine Structure

Cyclohexylamine

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

N-cyanocyclohexylamine Structure

N-cyanocyclohex...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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Structure

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

phenylcyanamide Structure

phenylcyanamide

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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Benzylamine Structure

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

benzylcyanamide Structure

benzylcyanamide

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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n-butylamine Structure

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

N/A Structure

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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2-Pyrimidinethiol (9CI) Structure

2-Pyrimidinethi...

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

Thiocyanic acid, 2-pyrimidinyl ester (7CI,9CI) Structure

Thiocyanic acid...

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N-Methylbenzylamine Structure

N-Methylbenzylamine

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~0%

N-benzyl-N-methyl cyanamide Structure

N-benzyl-N-meth...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

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4-Aminothiophenol Structure

4-Aminothiophenol

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~84%

4-amino phenyl thiocyanate Structure

4-amino phenyl ...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

Learn More

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

4-Aminothiophenol Structure

4-Aminothiophenol

~76%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

4-amino phenyl thiocyanate Structure

4-amino phenyl ...

Learn More

4-Mercaptophenol Structure

4-Mercaptophenol

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~84%

p-Thiocyanatophenol, p-thiocyanato Structure

p-Thiocyanatoph...

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

Learn More

4-Mercaptophenol Structure

4-Mercaptophenol

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~79%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

p-Thiocyanatophenol, p-thiocyanato Structure

p-Thiocyanatoph...

Learn More

4-Aminophenol Structure

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

N/A Structure

Learn More

4-Mercaptophenol Structure

4-Mercaptophenol

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

p-Thiocyanatophenol, p-thiocyanato Structure

p-Thiocyanatoph...

Learn More

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

4-Aminothiophenol Structure

4-Aminothiophenol

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

4-amino phenyl thiocyanate Structure

4-amino phenyl ...

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Cyclohexylamine Structure

Cyclohexylamine

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

N-cyanocyclohexylamine Structure

N-cyanocyclohex...

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Structure

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

phenylcyanamide Structure

phenylcyanamide

Learn More

2-Pyrimidinethiol (9CI) Structure

2-Pyrimidinethi...

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

Thiocyanic acid, 2-pyrimidinyl ester (7CI,9CI) Structure

Thiocyanic acid...

Learn More

2-Pyrimidinethiol (9CI) Structure

2-Pyrimidinethi...

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~87%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

Thiocyanic acid, 2-pyrimidinyl ester (7CI,9CI) Structure

Thiocyanic acid...

Learn More

2-Pyrimidinethiol (9CI) Structure

2-Pyrimidinethi...

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~78%

4-Chloro-5-Methoxypyridazin-3(2H)-One Structure

4-Chloro-5-Meth...

Thiocyanic acid, 2-pyrimidinyl ester (7CI,9CI) Structure

Thiocyanic acid...

Learn More

2-Phenylethanethiol Structure

2-Phenylethanethiol

2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one Structure

2-cyano-4-chlor...

~78%

2-phenylethyl thiocyanate Structure

2-phenylethyl t...

Learn More

2-Phenylethanethiol Structure

2-Phenylethanethiol

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~82%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

2-phenylethyl thiocyanate Structure

2-phenylethyl t...

Learn More

n-butylamine Structure

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

N/A Structure

Learn More

Benzylamine Structure

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

benzylcyanamide Structure

benzylcyanamide

Learn More

2-Phenylethanethiol Structure

2-Phenylethanethiol

2-cyano-4,5-dichloropyridazin-3(2H)-one Structure

2-cyano-4,5-dic...

~0%

4,5-Dichloro-3(2H)-pyridazinone Structure

4,5-Dichloro-3(...

2-phenylethyl thiocyanate Structure

2-phenylethyl t...

Learn More

An Efficient Approach for the Synthesis of N??1 Substituted ...

[Kumar, Vinod; Kaushik; Mazumdar, Avik European Journal of Organic Chemistry, 2008 , # 11 p. 1910 - 1916]

Copper (I)??Catalyzed Cascade Synthesis of 2??Arylsulfanyl??...

[Sahoo, Santosh K.; Jamir, Latonglila; Guin, Srimanta; Patel, Bhisma K. Advanced Synthesis and Catalysis, 2010 , vol. 352, # 14-15 p. 2538 - 2548]

In Silico Exploration for New Antimalarials: Arylsulfonyloxy...

[Lin, Chia-Chi; Hsieh, Tsung-Han; Liao, Pen-Yuan; Liao, Zhen-Yuan; Chang, Chih-Wei; Shih, Yu-Chiao; Yeh, Wen-Hsiung; Chien, Tun-Cheng Organic Letters, 2014 , vol. 16, # 3 p. 892 - 895]

Desulfurization and transformation of isothiocyanates to cya...

[Chen, Chun-Yen; Wong, Fung Fuh; Huang, Jiann-Jyh; Lin, Shao-Kai; Yeh, Mou-Yung Tetrahedron Letters, 2008 , vol. 49, # 46 p. 6505 - 6507]

Some Practical Methods for the Application of 5-Metallo-1-be...

[Wiedemann, Sean H.; Bio, Matthew M.; Brown, Liane M.; Hansen, Karl B.; Langille, Neil F. Synlett, 2012 , vol. 23, # 15 p. 2231 - 2236]