Organic & biomolecular chemistry

New methodology for the N-alkylation of 2-amino-3-acylthiophenes

L Aurelio, BL Flynn, PJ Scammells

Index: Aurelio, Luigi; Flynn, Bernard L.; Scammells, Peter J. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 13 p. 4886 - 4902

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Citation Number: 6

Abstract

2-Amino-3-acylthiophenes are known to allosterically modulate the A1adenosine receptor and are also used as intermediates in the synthesis of therapeutic agents and pharmacophores such as thienoazepines and thienopyrimidines. The N-alkylation of 2- aminothiophenes has been notoriously difficult to accomplish under mild conditions and there are very few examples of N-alkylated 2-aminothiophenes in the literature, all of ...

 Related Synthetic Route
ethyl 2-((((4-methoxybenzyl)oxy)carbonyl)(prop-2-yn-1-yl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-45-9

ethyl 2-((((4-m...

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-51-7

N/A

N/A Structure

1315321-47-1

N/A

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-52-8

N/A

N/A Structure

1315321-54-0

N/A

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

ethyl 2-(isopropylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-55-1

ethyl 2-(isopro...

ethyl 2-(ethyl(((4-methoxybenzyl)oxy)carbonyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-41-5

ethyl 2-(ethyl(...

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

893005-96-4

N/A

ethyl 2-((((4-methoxybenzyl)oxy)carbonyl)(propyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-42-6

ethyl 2-((((4-m...

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-48-2

N/A

N/A Structure

1315321-43-7

N/A

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-49-3

N/A

ethyl 2-(allyl(((4-methoxybenzyl)oxy)carbonyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-44-8

ethyl 2-(allyl(...

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-50-6

N/A

ethyl 2-((((4-methoxybenzyl)oxy)carbonyl)(methyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-40-4

ethyl 2-((((4-m...

~0%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

Ethyl 2-(methylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

893005-88-4

Ethyl 2-(methyl...

4-Methoxybenzylchloride Structure

824-94-2

4-Methoxybenzyl...

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

Ethyl 2-(methylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

893005-88-4

Ethyl 2-(methyl...

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-48-2

N/A

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

893005-96-4

N/A

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-49-3

N/A

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-50-6

N/A

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-51-7

N/A

N/A Structure

1315321-39-1

N/A

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

ethyl 2-(isopropylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate Structure

1315321-55-1

ethyl 2-(isopro...

N/A Structure

1315321-39-1

N/A

Benzyl bromide Structure

100-39-0

Benzyl bromide

~%

1-methoxy-2-[(4-methoxyphenyl)methyl]-4-methylbenzene Structure

53039-57-9

1-methoxy-2-[(4...

N/A Structure

1315321-52-8

N/A

ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Structure

4506-71-2

ETHYL 2-AMINO-4...

Ethanoic anhydride Structure

108-24-7

Ethanoic anhydride

~97%

Benzo(b)thiophene-3-carboxylic acid, 4,5,6,7-tetrahydro-2-(acetylamino)-, ethyl ester Structure

5919-29-9

Benzo(b)thiophe...


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