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.

 Related Synthetic Route
(4-MORPHOLINYLPHENYLMETHYL)BENZOTRIAZOL& Structure

120803-36-3

(4-MORPHOLINYLP...

lithium 1-phenylethenolate Structure

1052762-47-6

lithium 1-pheny...

~46%

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

6263-84-9

1,5-Pentanedion...

1H-Benzotriazole Structure

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1H-Benzotriazole

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N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

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21300-30-1

N/A

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

2-((phenylamino)methyl)cyclohexanone Structure

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N-(benzotriazol-1-ylmethyl)benzamide Structure

111184-75-9

N-(benzotriazol...

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21300-30-1

N/A

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

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1-(piperidin-1-ylmethyl)benzotriazole Structure

15622-20-5

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21300-30-1

N/A

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

Pimeclone Structure

534-84-9

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

120802-85-9

1-(1-morpholino...

N/A Structure

21300-30-1

N/A

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

2-(1-morpholinocyclohexyl)cyclohexanone Structure

127865-18-3

2-(1-morpholino...

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N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

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lithium enolate of 1-tetralone Structure

74074-96-7

lithium enolate...

~0%

1H-Benzotriazole Structure

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1H-Benzotriazole

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

127865-12-7

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

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(4-MORPHOLINYLPHENYLMETHYL)BENZOTRIAZOL& Structure

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(4-MORPHOLINYLP...

lithium 1-phenylethenolate Structure

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lithium 1-pheny...

~0%

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

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

120802-85-9

1-(1-morpholino...

lithium 1-phenylethenolate Structure

1052762-47-6

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

Ethanone,2-cyclohexylidene-1-phenyl Structure

5452-52-8

Ethanone,2-cycl...

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N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

62001-29-0

N-PHENYLBENZOTR...

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

56614-22-3

lithium 1,7,7-t...

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

1212073-07-8

1,7,7-trimethyl...

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1-(piperidin-1-ylmethyl)benzotriazole Structure

15622-20-5

1-(piperidin-1-...

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

56614-22-3

lithium 1,7,7-t...

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

28238-80-4

1,7,7-trimethyl...

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1-(piperidin-1-ylmethyl)benzotriazole Structure

15622-20-5

1-(piperidin-1-...

lithium 1-phenylethenolate Structure

1052762-47-6

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

90548-89-3

1-phenyl-3-pipe...

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N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

62001-29-0

N-PHENYLBENZOTR...

lithium 1-phenylethenolate Structure

1052762-47-6

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

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1H-Benzotriazole

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

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1-Propanone,1-p...

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N-(benzotriazol-1-ylmethyl)benzamide Structure

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N-(benzotriazol...

N/A Structure

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N/A

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

71666-57-4

N-[(2-oxocycloh...

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

127865-14-9

1-(2-METHYLPHEN...

N/A Structure

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N/A

~%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

2-(1-morpholinoethyl)cyclohexanone Structure

306993-95-3

2-(1-morpholino...

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N/A Structure

127865-15-0

N/A

N/A Structure

21300-30-1

N/A

~%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

N/A Structure

306993-94-2

N/A

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

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N/A

~%

1H-Benzotriazole Structure

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2-Benzylidenecyclohexanone Structure

5682-83-7

2-Benzylidenecy...

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

120802-85-9

1-(1-morpholino...

lithium 1-phenylethenolate Structure

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lithium 1-pheny...

~0%

1H-Benzotriazole Structure

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Ethanone,2-cyclohexylidene-1-phenyl Structure

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Ethanone,2-cycl...

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1-(piperidin-1-ylmethyl)benzotriazole Structure

15622-20-5

1-(piperidin-1-...

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N/A

~67%

1H-Benzotriazole Structure

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Pimeclone Structure

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Pimeclone

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N-PHENYLBENZOTRIAZOLEMETHANAMINE Structure

62001-29-0

N-PHENYLBENZOTR...

lithium 1-phenylethenolate Structure

1052762-47-6

lithium 1-pheny...

~9%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

2983-48-4

1-Propanone,1-p...

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1-(piperidin-1-ylmethyl)benzotriazole Structure

15622-20-5

1-(piperidin-1-...

lithium 1-phenylethenolate Structure

1052762-47-6

lithium 1-pheny...

~0%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

90548-89-3

1-phenyl-3-pipe...

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N-(benzotriazol-1-ylmethyl)benzamide Structure

111184-75-9

N-(benzotriazol...

N/A Structure

21300-30-1

N/A

~87%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

71666-57-4

N-[(2-oxocycloh...

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N-(benzotriazol-1-ylmethyl)benzamide Structure

111184-75-9

N-(benzotriazol...

N/A Structure

21300-30-1

N/A

~13%

1H-Benzotriazole Structure

95-14-7

1H-Benzotriazole

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

71666-57-4

N-[(2-oxocycloh...

Detail Learn More

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