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An Improved Synthesis of 1, 2, 3, 4-Tetrahydroisoquinolines via Intramolecular Cyclization of N-Acyl-N-(aryl) methyl-2-(phenylsulfinyl) ethylamine by Pummerer …

T Shinohara, J Toda, T Sano

Index: Shinohara, Tatsumi; Toda, Jun; Sano, Takehiro Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 5 p. 813 - 819

Full Text: HTML

Citation Number: 34

Abstract

Pummerer reaction of the sulfoxides 5 of N-acyl-N-(aryl) methyl-2-(phenylthio) ethylamines (4) on treatment with trifluoroacetic anhydride (TFAA) effectively caused intramolecular cyclization under a mild condition to give N-acyl-4-phenylthio-1, 2, 3, 4- tetrahydroisoquinolines (TIQs)(7). The reaction of the N-formyl sulfoxide 5c without a methoxy group in the benzene ring using a formyl group for N-protection is particularly ...

 Related Synthetic Route
N/A Structure

148679-35-0

N/A

~%

N-[2-(benzenesulfinyl)ethyl]-N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

148679-46-3

N-[2-(benzenesu...

Ethanamine,2-(phenylthio)- Structure

2014-75-7

Ethanamine,2-(p...

~%

N-[2-(benzenesulfinyl)ethyl]-N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

148679-46-3

N-[2-(benzenesu...

veratraldehyde Structure

120-14-9

veratraldehyde

~%

N-[2-(benzenesulfinyl)ethyl]-N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

148679-46-3

N-[2-(benzenesu...

1,2,3,4-tetrahydro-2-formyl-4-phenylthioisoquinoline Structure

191545-92-3

1,2,3,4-tetrahy...

~71%

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

benzylidene-(2-phenylsulfanyl-ethyl)-amine Structure

66859-95-8

benzylidene-(2-...

~%

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

N-benzyl-2-phenylsulfanylethanamine Structure

67747-34-6

N-benzyl-2-phen...

~%

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

N/A Structure

191545-79-6

N/A

~%

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

N-benzyl-N-formyl-2-(phenylthio)ethylamine Structure

191545-73-0

N-benzyl-N-form...

~%

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

~91%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

benzylidene-(2-phenylsulfanyl-ethyl)-amine Structure

66859-95-8

benzylidene-(2-...

~%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

N-benzyl-2-phenylsulfanylethanamine Structure

67747-34-6

N-benzyl-2-phen...

~%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

1,2,3,4-tetrahydro-2-formyl-4-phenylthioisoquinoline Structure

191545-92-3

1,2,3,4-tetrahy...

~%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

N/A Structure

191545-79-6

N/A

~%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

N-benzyl-N-formyl-2-(phenylthio)ethylamine Structure

191545-73-0

N-benzyl-N-form...

~%

2-methyl-1,2,3,4-tetrahydroisoquinoline Structure

1612-65-3

2-methyl-1,2,3,...

benzylidene-(2-phenylsulfanyl-ethyl)-amine Structure

66859-95-8

benzylidene-(2-...

~%

N-benzyl-2-phenylsulfanylethanamine Structure

67747-34-6

N-benzyl-2-phen...

Ethanamine,2-(phenylthio)- Structure

2014-75-7

Ethanamine,2-(p...

~%

N-benzyl-2-phenylsulfanylethanamine Structure

67747-34-6

N-benzyl-2-phen...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

N-benzyl-2-phenylsulfanylethanamine Structure

67747-34-6

N-benzyl-2-phen...

N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINE Structure

1699-52-1

N-FORMYL-1,2,3,...

~95%

1,2,3,4-Tetrahydroisoquinoline Structure

91-21-4

1,2,3,4-Tetrahy...

6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinecarbaldehyde Structure

96624-17-8

6,7-dimethoxy-3...

~99%

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

1745-07-9

6,7-Dimethoxy-1...

N-(carbobenzyloxy)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

191545-97-8

N-(carbobenzylo...

~89%

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

1745-07-9

6,7-Dimethoxy-1...

1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one Structure

26163-70-2

1-(6,7-dimethox...

~78%

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

1745-07-9

6,7-Dimethoxy-1...

1,2,3,4-tetrahydro-2-benzyloxycarbonyl-4-phenylthioisoquinoline Structure

191545-91-2

1,2,3,4-tetrahy...

~58%

benzyl 3,4-dihydro-1H-isoquinoline-2-carboxylate Structure

142266-67-9

benzyl 3,4-dihy...

benzylidene-(2-phenylsulfanyl-ethyl)-amine Structure

66859-95-8

benzylidene-(2-...

~%

benzyl 3,4-dihydro-1H-isoquinoline-2-carboxylate Structure

142266-67-9

benzyl 3,4-dihy...

N-benzyl-2-phenylsulfanylethanamine Structure

67747-34-6

N-benzyl-2-phen...

~%

benzyl 3,4-dihydro-1H-isoquinoline-2-carboxylate Structure

142266-67-9

benzyl 3,4-dihy...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

benzyl 3,4-dihydro-1H-isoquinoline-2-carboxylate Structure

142266-67-9

benzyl 3,4-dihy...

N/A Structure

191545-72-9

N/A

~%

benzyl 3,4-dihydro-1H-isoquinoline-2-carboxylate Structure

142266-67-9

benzyl 3,4-dihy...

N-benzyloxycarbonyl-N-benzyl-2-(phenylsulfinyl)ethylamine Structure

191545-78-5

N-benzyloxycarb...

~%

benzyl 3,4-dihydro-1H-isoquinoline-2-carboxylate Structure

142266-67-9

benzyl 3,4-dihy...

N-(carbobenzyloxy)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

191545-97-8

N-(carbobenzylo...

~97%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinecarbaldehyde Structure

96624-17-8

6,7-dimethoxy-3...

~85%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

N/A Structure

148679-35-0

N/A

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

veratraldehyde Structure

120-14-9

veratraldehyde

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

N/A Structure

191545-70-7

N/A

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

N/A Structure

191545-89-8

N/A

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

N-formyl-N-(3,4-dimethoxyphenyl)methyl-2-(phenylsulfinyl)ethylamine Structure

191545-76-3

N-formyl-N-(3,4...

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

N-benzyloxycarbonyl-N-(3,4-dimethoxyphenyl)methyl-2-(phenylthio)ethylamine Structure

191545-69-4

N-benzyloxycarb...

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

N/A Structure

191545-74-1

N/A

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

1,2,3,4-tetrahydro-2-benzyloxycarbonyl-6,7-dimethoxy-4-phenylthioisoquinoline Structure

191545-88-7

1,2,3,4-tetrahy...

~%

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...


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