Tetrahedron

Application of directed metalation in synthesis. Part 4: Expedient synthesis of substituted benzo [b] thiophene and naphthothiophene

C Mukherjee, S Kamila, A De

Index: Mukherjee, Chandrani; Kamila, Sukanta; De, Asish Tetrahedron, 2003 , vol. 59, # 26 p. 4767 - 4774

Full Text: HTML

Citation Number: 29

Abstract

A short, simple and inexpensive synthesis of several diversely substituted benzo [b] thiophenes and one naphthothiophene is described. The method involves introduction of methylsulfanyl group ortho-to the amide function of readily available N, N-diethylamides of aryl carboxylic acid by directed metalation. Thioindoxyls, obtained in high yields through side-chain deprotonation and cyclisation in one pot, are reduced to benzo [b] thiophene or ...

 Related Synthetic Route
Benzo[b]thiophen-3(2H)-one Structure

130-03-0

Benzo[b]thiophe...

~67%

Thianaphthene Structure

95-15-8

Thianaphthene

N,N-diethyl-2-methylsulfanyl-5-methoxy-6-trimethylsilylbenzamide Structure

121424-95-1

N,N-diethyl-2-m...

~89%

N,N-diethyl-5-methoxy-2-methylsulfanylbenzamide Structure

121425-05-6

N,N-diethyl-5-m...

N,N-diethyl-3-methoxy-2-trimethylsilylbenzamide Structure

85370-85-0

N,N-diethyl-3-m...

~%

N,N-diethyl-5-methoxy-2-methylsulfanylbenzamide Structure

121425-05-6

N,N-diethyl-5-m...

2,3-dihydro-4-methoxybenzo[b]thiophen-3-one Structure

220418-03-1

2,3-dihydro-4-m...

~82%

4-methoxy-1-benzothiophene Structure

3781-90-6

4-methoxy-1-ben...

Benzamide,N,N-diethyl-2-methoxy- Structure

51674-10-3

Benzamide,N,N-d...

~%

4-methoxy-1-benzothiophene Structure

3781-90-6

4-methoxy-1-ben...

N,N-diethyl-2-methoxy-6-methylsulfanylbenzamide Structure

596805-18-4

N,N-diethyl-2-m...

~%

4-methoxy-1-benzothiophene Structure

3781-90-6

4-methoxy-1-ben...

2,3-dihydro-6-methylbenzo[b]thiophen-3-one Structure

68670-98-4

2,3-dihydro-6-m...

~93%

6-Methylbenzo[b]thiophene Structure

16587-47-6

6-Methylbenzo[b...

N,N-diethyl-2-methylsulfanyl-4-methoxybenzamide Structure

596805-19-5

N,N-diethyl-2-m...

~75%

6-methoxybenzo[b]thiophen-3(2H)-one Structure

5858-22-0

6-methoxybenzo[...

Benzamide,N,N-diethyl-4-methoxy- Structure

7465-86-3

Benzamide,N,N-d...

~%

6-methoxybenzo[b]thiophen-3(2H)-one Structure

5858-22-0

6-methoxybenzo[...

2,3-dihydro-5-methoxybenzo[b]thiophen-3-one Structure

72002-19-8

2,3-dihydro-5-m...

~79%

5-Methoxy-1-benzothiophene Structure

20532-30-3

5-Methoxy-1-ben...

Dimethyl disulfide Structure

624-92-0

Dimethyl disulfide

N,N-diethyl-3-methoxybenzamide Structure

62924-93-0

N,N-diethyl-3-m...

~82%

N,N-diethyl-3-methoxy-2-methylsulfanylbenzamide Structure

596805-20-8

N,N-diethyl-3-m...

Dimethyl disulfide Structure

624-92-0

Dimethyl disulfide

Benzamide,2-chloro-N,N-diethyl- Structure

10345-79-6

Benzamide,2-chl...

~75%

2-chloro-N,N-diethyl-6-methylsulfanylbenzamide Structure

596805-22-0

2-chloro-N,N-di...

N,N-diethyl-2-methylsulfanylbenzamide Structure

65935-87-7

N,N-diethyl-2-m...

~67%

Benzo[b]thiophen-3(2H)-one Structure

130-03-0

Benzo[b]thiophe...

6-methoxybenzo[b]thiophen-3(2H)-one Structure

5858-22-0

6-methoxybenzo[...

~73%

6-Methoxy-1-benzothiophene Structure

90560-10-4

6-Methoxy-1-ben...

Benzamide,N,N-diethyl-4-methoxy- Structure

7465-86-3

Benzamide,N,N-d...

~%

6-Methoxy-1-benzothiophene Structure

90560-10-4

6-Methoxy-1-ben...

N,N-diethyl-2-methylsulfanyl-4-methoxybenzamide Structure

596805-19-5

N,N-diethyl-2-m...

~%

6-Methoxy-1-benzothiophene Structure

90560-10-4

6-Methoxy-1-ben...

2,3-dihydro-7-methoxybenzo[b]thiophen-3-one Structure

72002-20-1

2,3-dihydro-7-m...

~73%

7-METHOXYBENZO[B]THIOPHENE Structure

88791-08-6

7-METHOXYBENZO[...

2,3-dihydro-4,6-dimethoxybenzo[b]thiophen-3-one Structure

438210-93-6

2,3-dihydro-4,6...

~83%

4,6-dimethoxy-1-benzothiophene Structure

346592-25-4

4,6-dimethoxy-1...


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