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

The synthesis of all of the monomethyl isomers of benzo [b] naphtho [1, 2??d] thiophene

Y Tominaga, R Pratap, RN Castle…

Index: Tominaga, Yoshinori; Pratap, Ram; Castle, Raymond N.; Lee, Milton L. Journal of Heterocyclic Chemistry, 1982 , vol. 19, p. 871 - 877

Full Text: HTML

Citation Number: 23

Abstract

Jul-Aug 1982 Monomethyl Isomers of Benzo[o]naphtho[l,2-c/]thiophene 873 were readily prepared from o- and /»-methylbenzenethiol via the method of Tilak (5). However, in the case of m-methylbenzenethiol, this reaction gave a mixture of 4-methyl- and 6-methylbenzo[6]thiophene -2-carbox- aldehyde (34 and 35). When this mixture was allowed to react with 30 in a similar manner, a mixture of two styryl compounds, 4-methyl- and 6-methyl-2-styrylbenzo[6]thio- ...

2-(α-methylstyryl)benzo[b]thiophene Structure

2-(α-methylstyr...

~68%

6-methylnaphtho[2,1-b][1]benzothiole Structure

6-methylnaphtho...

2-CHLOROMETHYL-BENZO[B]THIOPHENE Structure

2-CHLOROMETHYL-...

~%

2-[2-(2-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(2-methylp...

Triphenylphosphine Structure

Triphenylphosphine

~%

2-[2-(2-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(2-methylp...

(1-benzothien-2-ylmethyl)(triphenyl)phosphonium chloride Structure

(1-benzothien-2...

2-Methylbenzaldehyde Structure

2-Methylbenzaldehyde

~%

2-[2-(2-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(2-methylp...

2-(diethoxyphosphorylmethyl)-1-benzothiophene Structure

2-(diethoxyphos...

2-Methylbenzaldehyde Structure

2-Methylbenzaldehyde

~%

2-[2-(2-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(2-methylp...

Diethyl benzylphosphonate Structure

Diethyl benzylp...

7-methyl-1-benzothiophene-2-carbaldehyde Structure

7-methyl-1-benz...

~%

7-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

7-methyl-2-(2-p...

5-Methylbenzo[b]thiophene-2-carbaldehyde Structure

5-Methylbenzo[b...

Diethyl benzylphosphonate Structure

Diethyl benzylp...

~%

5-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

5-methyl-2-(2-p...

5-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

5-methyl-2-(2-p...

~43%

10-methylnaphtho[2,1-b][1]benzothiole Structure

10-methylnaphth...

2-CHLOROMETHYL-BENZO[B]THIOPHENE Structure

2-CHLOROMETHYL-...

~%

2-[2-(3-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(3-methylp...

Triphenylphosphine Structure

Triphenylphosphine

~%

2-[2-(3-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(3-methylp...

Benzo[b]thiophene-2-carboxaldehyde Structure

Benzo[b]thiophe...

Diethyl (4-Methylbenzyl)phosphonate Structure

Diethyl (4-Meth...

~%

2-[2-(3-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(3-methylp...

(1-benzothien-2-ylmethyl)(triphenyl)phosphonium chloride Structure

(1-benzothien-2...

m-Tolualdehyde Structure

~%

2-[2-(3-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(3-methylp...

2-(diethoxyphosphorylmethyl)-1-benzothiophene Structure

2-(diethoxyphos...

m-Tolualdehyde Structure

~%

2-[2-(3-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(3-methylp...

2-CHLOROMETHYL-BENZO[B]THIOPHENE Structure

2-CHLOROMETHYL-...

~%

2-[2-(4-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(4-methylp...

Triphenylphosphine Structure

Triphenylphosphine

~%

2-[2-(4-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(4-methylp...

Benzo[b]thiophene-2-carboxaldehyde Structure

Benzo[b]thiophe...

Diethyl (3-Methylbenzyl)phosphonate Structure

Diethyl (3-Meth...

~%

2-[2-(4-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(4-methylp...

p-Tolualdehyde Structure

(1-benzothien-2-ylmethyl)(triphenyl)phosphonium chloride Structure

(1-benzothien-2...

~%

2-[2-(4-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(4-methylp...

p-Tolualdehyde Structure

2-(diethoxyphosphorylmethyl)-1-benzothiophene Structure

2-(diethoxyphos...

~%

2-[2-(4-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(4-methylp...

2-[2-(2-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(2-methylp...

~41%

4-methylnaphtho[2,1-b][1]benzothiole Structure

4-methylnaphtho...

6-Methylbenzo[b]thiophene-2-carboxylic acid Structure

6-Methylbenzo[b...

~%

6-methyl-1-benzothiophene-2-carbaldehyde Structure

6-methyl-1-benz...

3-chloro-2-hydroxymethyl-4-methylbenzo[b]thiophene Structure

3-chloro-2-hydr...

~75%

3-chloro-4-methyl-1-benzothiophene-2-carbaldehyde Structure

3-chloro-4-meth...

3-Chloro-4-methyl-1-benzothiophene-2-carbonyl chloride Structure

3-Chloro-4-meth...

~%

3-chloro-4-methyl-1-benzothiophene-2-carbaldehyde Structure

3-chloro-4-meth...

715567 Structure

~52%

3-Chloro-4-methyl-1-benzothiophene-2-carbonyl chloride Structure

3-Chloro-4-meth...

3-chloro-2-hydroxymethyl-4-methylbenzo[b]thiophene Structure

3-chloro-2-hydr...

~%

3-chloro-4-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

3-chloro-4-meth...

3-Chloro-4-methyl-1-benzothiophene-2-carbonyl chloride Structure

3-Chloro-4-meth...

~%

3-chloro-4-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

3-chloro-4-meth...

Diethyl benzylphosphonate Structure

Diethyl benzylp...

3-chloro-4-methyl-1-benzothiophene-2-carbaldehyde Structure

3-chloro-4-meth...

~%

3-chloro-4-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

3-chloro-4-meth...

3-chloro-4-methyl-2-(2-phenylethenyl)-1-benzothiophene Structure

3-chloro-4-meth...

~35%

11-methylnaphtho[2,1-b][1]benzothiole Structure

11-methylnaphth...

3-chloro-4-methyl-1-benzothiophene-2-carbaldehyde Structure

3-chloro-4-meth...

~%

11-methylnaphtho[2,1-b][1]benzothiole Structure

11-methylnaphth...

3-chloro-2-hydroxymethyl-4-methylbenzo[b]thiophene Structure

3-chloro-2-hydr...

~%

11-methylnaphtho[2,1-b][1]benzothiole Structure

11-methylnaphth...

3-Chloro-4-methyl-1-benzothiophene-2-carbonyl chloride Structure

3-Chloro-4-meth...

~%

11-methylnaphtho[2,1-b][1]benzothiole Structure

11-methylnaphth...

2-[2-(4-methylphenyl)ethenyl]-1-benzothiophene Structure

2-[2-(4-methylp...

~44%

2-methylnaphtho[2,1-b][1]benzothiole Structure

2-methylnaphtho...