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

Tetrahedron

Benzotriazole-assisted synthesis of novel mannich bases from ketones and diverse aldehydes

AR Katritzky, PA Harris

Index: Katritzky, Alan R.; Harris, Philip A. Tetrahedron, 1990 , vol. 46, # 3 p. 987 - 996

Full Text: HTML

Citation Number: 50

Abstract

A wide variety of β-amino ketones are prepared in moderate to good yields by the reaction of the lithium enolates of cyclohexanone, acetophenone, α-tetralone and camphor with the readily available adducts from an aldehyde or ketone, an amine and benzotriazole. Some diastereoselectivity is observed when the benzotriazole adduct is derived from benzaldehyde.

(4-MORPHOLINYLPHENYLMETHYL)BENZOTRIAZOL& Structure

(4-MORPHOLINYLP...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~46%

1,5-Pentanedione,1,3,5-triphenyl- Structure

1,5-Pentanedion...

1H-Benzotriazole Structure

1H-Benzotriazole

N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

N-PHENYLBENZOTR...

N/A Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

2-((phenylamino)methyl)cyclohexanone Structure

2-((phenylamino...

N-(benzotriazol-1-ylmethyl)benzamide Structure

N-(benzotriazol...

N/A Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

N-[(2-oxocyclohexyl)methyl]benzamide Structure

N-[(2-oxocycloh...

1-(piperidin-1-ylmethyl)benzotriazole Structure

1-(piperidin-1-...

N/A Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Pimeclone Structure

1-(1-morpholinocyclohexyl)-1H-1,2,3-benzotriazole Structure

1-(1-morpholino...

N/A Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

2-(1-morpholinocyclohexyl)cyclohexanone Structure

2-(1-morpholino...

N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

N-PHENYLBENZOTR...

lithium enolate of 1-tetralone Structure

lithium enolate...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

3,4-dihydro-2-(phenylaminomethyl)-1-naphthalenone Structure

3,4-dihydro-2-(...

Detail

(4-MORPHOLINYLPHENYLMETHYL)BENZOTRIAZOL& Structure

(4-MORPHOLINYLP...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~0%

1,5-Pentanedione,1,3,5-triphenyl- Structure

1,5-Pentanedion...

1H-Benzotriazole Structure

1H-Benzotriazole

1-(1-morpholinocyclohexyl)-1H-1,2,3-benzotriazole Structure

1-(1-morpholino...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Ethanone,2-cyclohexylidene-1-phenyl- Structure

Ethanone,2-cycl...

Detail

N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

N-PHENYLBENZOTR...

lithium 1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-olate Structure

lithium 1,7,7-t...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

1,7,7-trimethyl-3-(phenylaminomethyl)-bicyclo(2.2.1)heptan-2-one Structure

1,7,7-trimethyl...

1-(piperidin-1-ylmethyl)benzotriazole Structure

1-(piperidin-1-...

lithium 1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-olate Structure

lithium 1,7,7-t...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

1,7,7-trimethyl-3-(piperidinomethyl)-bicyclo(2.2.1)heptan-2-one Structure

1,7,7-trimethyl...

1-(piperidin-1-ylmethyl)benzotriazole Structure

1-(piperidin-1-...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

1-phenyl-3-piperidin-1-yl-2-(piperidin-1-ylmethyl)propan-1-one Structure

1-phenyl-3-pipe...

Detail

N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

N-PHENYLBENZOTR...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

1-Propanone,1-phenyl-3-(phenylamino)- Structure

1-Propanone,1-p...

N-(benzotriazol-1-ylmethyl)benzamide Structure

N-(benzotriazol...

N/A Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

N-[(2-oxocyclohexyl)methyl]benzamide Structure

N-[(2-oxocycloh...

Detail

1-(2-METHYLPHENOXY)-2-PROPANOL Structure

1-(2-METHYLPHEN...

N/A Structure

~%

1H-Benzotriazole Structure

1H-Benzotriazole

2-(1-morpholinoethyl)cyclohexanone Structure

2-(1-morpholino...

N/A Structure

N/A Structure

~%

1H-Benzotriazole Structure

1H-Benzotriazole

N/A Structure

N-[α-(benzotriazol-1-yl)phenylmethyl]piperidine Structure

N-[α-(benzotria...

N/A Structure

~%

1H-Benzotriazole Structure

1H-Benzotriazole

2-Benzylidenecyclohexanone Structure

2-Benzylidenecy...

Detail

1-(1-morpholinocyclohexyl)-1H-1,2,3-benzotriazole Structure

1-(1-morpholino...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Ethanone,2-cyclohexylidene-1-phenyl- Structure

Ethanone,2-cycl...

Detail

1-(piperidin-1-ylmethyl)benzotriazole Structure

1-(piperidin-1-...

N/A Structure

~67%

1H-Benzotriazole Structure

1H-Benzotriazole

Pimeclone Structure

N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

N-PHENYLBENZOTR...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~9%

1H-Benzotriazole Structure

1H-Benzotriazole

1-Propanone,1-phenyl-3-(phenylamino)- Structure

1-Propanone,1-p...

1-(piperidin-1-ylmethyl)benzotriazole Structure

1-(piperidin-1-...

lithium 1-phenylethenolate Structure

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

1-phenyl-3-piperidin-1-yl-2-(piperidin-1-ylmethyl)propan-1-one Structure

1-phenyl-3-pipe...

Detail

N-(benzotriazol-1-ylmethyl)benzamide Structure

N-(benzotriazol...

N/A Structure

~87%

1H-Benzotriazole Structure

1H-Benzotriazole

N-[(2-oxocyclohexyl)methyl]benzamide Structure

N-[(2-oxocycloh...

N-(benzotriazol-1-ylmethyl)benzamide Structure

N-(benzotriazol...

N/A Structure

~13%

1H-Benzotriazole Structure

1H-Benzotriazole

N-[(2-oxocyclohexyl)methyl]benzamide Structure

N-[(2-oxocycloh...

Detail

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