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

Tetrahedron

Convenient approaches to heterocycles via copper-catalysed additions of organic polyhalides to activated olefins

P Martin, E Steiner, J Streith, T Winkler, D Bellš

Index: Martin, Pierre; Steiner, Eginhard; Streith, Jacques; Winkler, Tammo; Bellus, Daniel Tetrahedron, 1985 , vol. 41, # 19 p. 4057 - 4078

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Citation Number: 84

Abstract

An efficient method for the synthesis of 2, 3-dichloro-5-substituted (Cl, CF3, alkyl) pyridines 29 starting from the 1: 1 adducts of the copper-catalysed addition of chloral or the corresponding 2, 2-dichloroaldehydes to acrylonitrile is presented. Proper choice of experimental conditions allows the preparation of 29 in a one-pot process. Similarly, the CuCl-catalysed reaction of methyl itaconate with several trichloromethyl compounds R- ...

2,2-dichloro-3,3,3-trifluoro-propionaldehyde Structure

2,2-dichloro-3,...

Acrylonitrile Structure

~60%

2,3-Dichloro-5-(trifluoromethyl)pyridine Structure

2,3-Dichloro-5-...

Heptanal Structure

~45%

2,2-dichloroheptanal Structure

2,2-dichloroheptanal

2,3-dichloro-5-(pentachloroethyl)-pyridine Structure

2,3-dichloro-5-...

~66%

2,3-dichloro-5-(2,2-dichloro-1,1,2-trifluoroethyl)pyridine Structure

2,3-dichloro-5-...

2,3-dichloro-5-(2,2,2-trichloroethyl)-pyridine Structure

2,3-dichloro-5-...

~%

2,3-dichloro-5-(2,2-dichloro-1,1,2-trifluoroethyl)pyridine Structure

2,3-dichloro-5-...

methyl 2-oxo-6-(trifluoromethyl)pyran-4-carboxylate Structure

methyl 2-oxo-6-...

Acetylene Structure

~91%

Methyl 3-(trifluoromethyl)benzoate Structure

Methyl 3-(trifl...

methyl 2-oxo-6-(trifluoromethyl)pyran-4-carboxylate Structure

methyl 2-oxo-6-...

Norbornadiene Structure

~85%

Methyl 3-(trifluoromethyl)benzoate Structure

Methyl 3-(trifl...

ethene Structure

Chloral Structure

~67%

2,2,4-Trichlorobutanal Structure

2,2,4-Trichloro...

2,2-dichloropropanal Structure

2,2-dichloropropanal

Acrylonitrile Structure

~53%

2,5-Dichoro-3-picoline Structure

2,5-Dichoro-3-p...

Chloral Structure

Methacrylonitrile Structure

Methacrylonitrile

~63%

2,5-Dichoro-3-picoline Structure

2,5-Dichoro-3-p...

4-formyl-2-methyl-2,4,4-trichlorobutyronitrile Structure

4-formyl-2-meth...

~59%

2,5-Dichoro-3-picoline Structure

2,5-Dichoro-3-p...

Dimethyl itaconate Structure

Dimethyl itaconate

~%

Trimethyl trans-Aconitate Structure

Trimethyl trans...

Methanol Structure

6-chloro-4-methoxycarbonyl-2H-pyran-2-one Structure

6-chloro-4-meth...

~85%

Trimethyl trans-Aconitate Structure

Trimethyl trans...

methyl-3-methoxycarbonyl-3,5,5,5-tetrachloropentaneoate Structure

methyl-3-methox...

~%

Trimethyl trans-Aconitate Structure

Trimethyl trans...

dimethyl 2-(2,2-dichlorovinyl)but-2-enedioate Structure

dimethyl 2-(2,2...

~%

Trimethyl trans-Aconitate Structure

Trimethyl trans...

2,4,4-trichloro-5-oxopentanenitrile Structure

2,4,4-trichloro...

~89%

2,3,5-Trichloropyridine Structure

2,3,5-Trichloro...