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

Tetrahedron

Amides as precursors of imidoyl radicals in cyclisation reactions

…, AJ Fletcher, JM Pedersen, PJ Lovell, MRJ Elsegood…

Index: Bowman, W. Russell; Fletcher, Anthony J.; Pedersen, Jan M.; Lovell, Peter J.; Elsegood, Mark R.J.; Hernandez Lopez, Elena; McKee, Vickie; Potts, Graeme B.S. Tetrahedron, 2007 , vol. 63, # 1 p. 191 - 203

Full Text: HTML

Citation Number: 34

Abstract

Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have ...

ethyl 4-(2-formyl-1H-pyrrol-1-yl)butanoate Structure

ethyl 4-(2-form...

~%

4-(2-formylpyrrol-1-yl)butanoic acid Structure

4-(2-formylpyrr...

2-Formyl-1H-pyrrole Structure

2-Formyl-1H-pyrrole

~%

4-(2-formylpyrrol-1-yl)butanoic acid Structure

4-(2-formylpyrr...

METHYLMAGNESIUM BROMIDE Structure

METHYLMAGNESIUM...

Methyl 2-aminobenzoate Structure

Methyl 2-aminob...

~95%

2-(2-Aminophenyl)propan-2-ol Structure

2-(2-Aminopheny...

N/A Structure

~82%

3-butyl-2-methyl-1H-indole Structure

3-butyl-2-methy...

(Z)-phenyl N-[2-(cyclohexen-1-yl)phenyl]ethaneselenoimidate Structure

(Z)-phenyl N-[2...

~10%

6-methyl-7,8,9,10-tetrahydrophenanthridine Structure

6-methyl-7,8,9,...

Pyrrole-2-carbonitrile Structure

Pyrrole-2-carbo...

~%

4-(2-cyanopyrrol-1-yl)butanoic acid Structure

4-(2-cyanopyrro...

3-Cyanoindole Structure

~%

4-(3-cyanoindol-1-yl)butanoic acid Structure

4-(3-cyanoindol...

2′-Nitroacetophenone Structure

2′-Nitroacetophenone

methylidene triphenyl phosphorane Structure

methylidene tri...

~%

1-nitro-2-prop-1-en-2-ylbenzene Structure

1-nitro-2-prop-...

ethyl3-(2-aminophenyl)acrylate Structure

ethyl3-(2-amino...

~%

1H-Indole-3-aceticacid, 2-methyl-, ethyl ester Structure

1H-Indole-3-ace...

N/A Structure

~%

1H-Indole-3-aceticacid, 2-methyl-, ethyl ester Structure

1H-Indole-3-ace...

p-toluoyl chloride Structure

p-toluoyl chloride

Allylamine Structure

~93%

4-methyl-N-prop-2-enylbenzamide Structure

4-methyl-N-prop...

4-(3-cyanoindol-1-yl)butanoic acid Structure

4-(3-cyanoindol...

2-Phenylethanamine Structure

2-Phenylethanamine

~90%

4-(3-cyanoindol-1-yl)-N-(2-phenylethyl)butanamide Structure

4-(3-cyanoindol...

3-Cyanoindole Structure

~%

4-(3-cyanoindol-1-yl)-N-(2-phenylethyl)butanamide Structure

4-(3-cyanoindol...

4-(2-cyanopyrrol-1-yl)butanoic acid Structure

4-(2-cyanopyrro...

2-Phenylethanamine Structure

2-Phenylethanamine

~75%

4-(2-cyanopyrrol-1-yl)-N-(2-phenylethyl)butanamide Structure

4-(2-cyanopyrro...

Pyrrole-2-carbonitrile Structure

Pyrrole-2-carbo...

~%

4-(2-cyanopyrrol-1-yl)-N-(2-phenylethyl)butanamide Structure

4-(2-cyanopyrro...

N-(2-iodophenyl)formamide Structure

N-(2-iodophenyl...

~%

2-(cyclohexen-1-yl)aniline Structure

2-(cyclohexen-1...

Cyclohexanone Structure

~%

2-(cyclohexen-1-yl)aniline Structure

2-(cyclohexen-1...