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

Tetrahedron

Enamine Chemistry—XXIV.: Synthesis, thiation, and reduction of lactams

AA El-Barbary, S Carlsson, SO Lawesson

Index: El-Barbary, A. A.; Carlsson, S.; Lawesson, S.-O. Tetrahedron, 1982 , vol. 38, # 3 p. 405 - 412

Full Text: HTML

Citation Number: 20

Abstract

Enamines, 1, prepared from cyclohexanones or cyclopentanones are reacted with acrylamide to give lactams, the condensed 2-piperidones, 2. Ethyl 2-(1-pyrrolidinyl)-2- cyclohexene-1-propanoate, 3, when treated with primary amines, produces the corresponding N-substituted 2-piperidones, 4. Ethyl 2-(1-pyrrolidinyl)-2-cyclohexene-1- ethanoates and ethyl 2-(1-pyrrolidinyl)-2-cyclopentene-1-ethanoate, 5, react with primary ...

3,4,4a,5,6,7-hexahydro-2H-cyclopenta[b]pyridine Structure

3,4,4a,5,6,7-he...

Ethanoic anhydride Structure

Ethanoic anhydride

~90%

1-(2-azabicyclo[4.3.0]non-10-en-2-yl)ethanone Structure

1-(2-azabicyclo...

1-Pyrrolidino-1-cyclopentene Structure

1-Pyrrolidino-1...

~%

1-(2-azabicyclo[4.3.0]non-10-en-2-yl)ethanone Structure

1-(2-azabicyclo...

3,4,6,7-TETRAHYDRO-1H-CYCLOPENTA[B]PYRIDIN-2(5H)-ONE Structure

3,4,6,7-TETRAHY...

~%

1-(2-azabicyclo[4.3.0]non-10-en-2-yl)ethanone Structure

1-(2-azabicyclo...

1,3,4,5,6,7-hexahydro-2H-cyclopenta[b]pyridine-2-thione Structure

1,3,4,5,6,7-hex...

~%

1-(2-azabicyclo[4.3.0]non-10-en-2-yl)ethanone Structure

1-(2-azabicyclo...

3,4,6,7-TETRAHYDRO-1H-CYCLOPENTA[B]PYRIDIN-2(5H)-ONE Structure

3,4,6,7-TETRAHY...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

1-(2-azabicyclo[4.3.0]non-10-en-2-yl)ethanone Structure

1-(2-azabicyclo...

Ethanoic anhydride Structure

Ethanoic anhydride

1,3,4,5,6,7-hexahydro-2H-cyclopenta[b]pyridine-2-thione Structure

1,3,4,5,6,7-hex...

~%

1-(2-azabicyclo[4.3.0]non-10-en-2-yl)ethanone Structure

1-(2-azabicyclo...

2,3,4,4a,5,6,7,8-octahydroquinoline Structure

2,3,4,4a,5,6,7,...

Ethanoic anhydride Structure

Ethanoic anhydride

~92%

Ethanone,1-(3,4,5,6,7,8-hexahydro-1(2H)-quinolinyl)- Structure

Ethanone,1-(3,4...

1-pyrrolidinocyclohexene Structure

1-pyrrolidinocy...

~%

Ethanone,1-(3,4,5,6,7,8-hexahydro-1(2H)-quinolinyl)- Structure

Ethanone,1-(3,4...

3,4,5,6,7,8-HEXAHYDRO-2(1H)-QUINOLINONE Structure

3,4,5,6,7,8-HEX...

~%

Ethanone,1-(3,4,5,6,7,8-hexahydro-1(2H)-quinolinyl)- Structure

Ethanone,1-(3,4...

3,4,5,6,7,8-hexahydroquinoline-2(1H)-thione Structure

3,4,5,6,7,8-hex...

~%

Ethanone,1-(3,4,5,6,7,8-hexahydro-1(2H)-quinolinyl)- Structure

Ethanone,1-(3,4...

3,4,5,6,7,8-HEXAHYDRO-2(1H)-QUINOLINONE Structure

3,4,5,6,7,8-HEX...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

Ethanone,1-(3,4,5,6,7,8-hexahydro-1(2H)-quinolinyl)- Structure

Ethanone,1-(3,4...

Ethanoic anhydride Structure

Ethanoic anhydride

3,4,5,6,7,8-hexahydroquinoline-2(1H)-thione Structure

3,4,5,6,7,8-hex...

~%

Ethanone,1-(3,4,5,6,7,8-hexahydro-1(2H)-quinolinyl)- Structure

Ethanone,1-(3,4...

1-Pyrrolidino-1-cyclopentene Structure

1-Pyrrolidino-1...

Benzylamine Structure

~58%

N-benzylcyclopentanimine Structure

N-benzylcyclope...

1-pyrrolidinocyclohexene Structure

1-pyrrolidinocy...

Acrylamide Crystals Structure

Acrylamide Crystals

~%

3,4,5,6,7,8-HEXAHYDRO-2(1H)-QUINOLINONE Structure

3,4,5,6,7,8-HEX...

3,4,5,6,7,8-HEXAHYDRO-2(1H)-QUINOLINONE Structure

3,4,5,6,7,8-HEX...

~79%

2,3,4,4a,5,6,7,8-octahydroquinoline Structure

2,3,4,4a,5,6,7,...

3,4,5,6,7,8-hexahydroquinoline-2(1H)-thione Structure

3,4,5,6,7,8-hex...

~87%

2,3,4,4a,5,6,7,8-octahydroquinoline Structure

2,3,4,4a,5,6,7,...

1-Pyrrolidino-1-cyclopentene Structure

1-Pyrrolidino-1...

Monobromoacetanilide Structure

Monobromoacetanilide

~84%

N-phenyl-2-pyrrolidin-1-ylacetamide Structure

N-phenyl-2-pyrr...

1-pyrrolidinocyclohexene Structure

1-pyrrolidinocy...

Monobromoacetanilide Structure

Monobromoacetanilide

~82%

N-phenyl-2-pyrrolidin-1-ylacetamide Structure

N-phenyl-2-pyrr...

Enamine chemistry—XXV: Reduction of enaminones by LiAlH4 and...

[Carlsson, S.; Lawesson, S.-O. Tetrahedron, 1982 , vol. 38, # 3 p. 413 - 417]