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

The synthesis of dinaphthothiophenes

ML Tedjamulia, Y Tominaga…

Index: Tedjamulia, Marvin L.; Tominaga, Yoshinori; Castle, Raymond N.; Lee, Milton L. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 1143 - 1148

Full Text: HTML

Citation Number: 47

Abstract

Abstract The synthesis of dinaphtho [1, 2-b: 2′, 3′-d] thiophene (6), dinaphtho [2, 1-b: 2′, 3′-d] thiophene (15), dinaphtho-[1, 2-b: 1′, 2′-d] thiophene (20), dinaphtho [2, 1-b: 1′, 2′-d] thiophene (26), dinaphtho [2, 3-b: 2′, 3′-d] thiophene (37) and dinaphtho [1, 2-b: 2′, 1′-d] thiophene (45) has been accomplished.

2-(benzo[f][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[f][1]b...

~82%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[f][1]b...

Phthalic anhydride Structure

Phthalic anhydride

~%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[f][1]b...

Naphtho[2,3-b]thiophene Structure

Naphtho[2,3-b]t...

~%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[f][1]b...

1-naphthalen-1-ylsulfanylpropan-2-one Structure

1-naphthalen-1-...

~70%

3-methylbenzo[g][1]benzothiole Structure

3-methylbenzo[g...

1-Aminonaphthalene Structure

1-Aminonaphthalene

~%

3-methylbenzo[g][1]benzothiole Structure

3-methylbenzo[g...

ethyl 1-naphthyl xanthate Structure

ethyl 1-naphthy...

~%

3-methylbenzo[g][1]benzothiole Structure

3-methylbenzo[g...

1-NAPHTHALENETHIOL Structure

1-NAPHTHALENETHIOL

~%

3-methylbenzo[g][1]benzothiole Structure

3-methylbenzo[g...

Phthalic anhydride Structure

Phthalic anhydride

naphtho[1,2-b]thiophene Structure

naphtho[1,2-b]t...

~71%

2-(benzo[g][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[g][1]b...

2-(benzo[g][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[g][1]b...

~71%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[g][1]b...

Phthalic anhydride Structure

Phthalic anhydride

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[g][1]b...

naphtho[1,2-b]thiophene Structure

naphtho[1,2-b]t...

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[g][1]b...

2-(benzo[g][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[g][1]b...

~73%

[2-(benzo[g][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[g][1]...

Phthalic anhydride Structure

Phthalic anhydride

~%

[2-(benzo[g][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[g][1]...

naphtho[1,2-b]thiophene Structure

naphtho[1,2-b]t...

~%

[2-(benzo[g][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[g][1]...

2-(benzo[g][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[g][1]b...

~%

[2-(benzo[g][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[g][1]...

2-(benzo[f][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[f][1]b...

~83%

[2-(benzo[f][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[f][1]...

Phthalic anhydride Structure

Phthalic anhydride

~%

[2-(benzo[f][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[f][1]...

Naphtho[2,3-b]thiophene Structure

Naphtho[2,3-b]t...

~%

[2-(benzo[f][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[f][1]...

2-(benzo[f][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[f][1]b...

~%

[2-(benzo[f][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[f][1]...

[2-(benzo[f][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[f][1]...

~80%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[f][1]b...

Phthalic anhydride Structure

Phthalic anhydride

~%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[f][1]b...

Naphtho[2,3-b]thiophene Structure

Naphtho[2,3-b]t...

~%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[f][1]b...

2-(benzo[f][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[f][1]b...

~%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[f][1]b...

2-(benzo[f][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[f][1]b...

~%

2-(benzo[f][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[f][1]b...

Benzoic acid,2-(2-thienylcarbonyl)- Structure

Benzoic acid,2-...

~88%

Benzoic acid,2-(2-thienylmethyl)- Structure

Benzoic acid,2-...

[2-(benzo[g][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[g][1]...

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[g][1]b...

Phthalic anhydride Structure

Phthalic anhydride

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[g][1]b...

naphtho[1,2-b]thiophene Structure

naphtho[1,2-b]t...

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[g][1]b...

2-(benzo[g][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[g][1]b...

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[g][1]b...

2-(benzo[g][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[g][1]b...

~%

2-(benzo[g][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[g][1]b...

Phthalic anhydride Structure

Phthalic anhydride

naphtho[2,1-b]thiophene Structure

naphtho[2,1-b]t...

~70%

2-(benzo[e][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[e][1]b...

3-methylbenzo[g][1]benzothiole Structure

3-methylbenzo[g...

~%

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

1-NAPHTHALENETHIOL Structure

1-NAPHTHALENETHIOL

~%

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

1-naphthalen-1-ylsulfanylpropan-2-one Structure

1-naphthalen-1-...

~%

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

1-Aminonaphthalene Structure

1-Aminonaphthalene

~%

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

ethyl 1-naphthyl xanthate Structure

ethyl 1-naphthy...

~%

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

benzo[g][1]benzothiole-3-carbaldehyde Structure

benzo[g][1]benz...

Diethyl benzylphosphonate Structure

Diethyl benzylp...

~%

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

2-(benzo[f][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[f][1]b...

~74%

Dinaphtho[2,3-b,2',3-d]thiophene Structure

Dinaphtho[2,3-b...

2-(2-phenylethenyl)benzo[e][1]benzothiole Structure

2-(2-phenylethe...

~45%

Dinaphtho(2,1-b:1',2'-d)thiophene Structure

Dinaphtho(2,1-b...

2-(benzo[e][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[e][1]b...

~82%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[e][1]b...

Phthalic anhydride Structure

Phthalic anhydride

~%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[e][1]b...

naphtho[2,1-b]thiophene Structure

naphtho[2,1-b]t...

~%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[e][1]b...

2-(benzo[e][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[e][1]b...

~80%

[2-(benzo[e][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[e][1]...

Phthalic anhydride Structure

Phthalic anhydride

~%

[2-(benzo[e][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[e][1]...

naphtho[2,1-b]thiophene Structure

naphtho[2,1-b]t...

~%

[2-(benzo[e][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[e][1]...

2-(benzo[e][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[e][1]b...

~%

[2-(benzo[e][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[e][1]...

1-Aminonaphthalene Structure

1-Aminonaphthalene

~%

1-naphthalen-1-ylsulfanylpropan-2-one Structure

1-naphthalen-1-...

ethyl 1-naphthyl xanthate Structure

ethyl 1-naphthy...

~%

1-naphthalen-1-ylsulfanylpropan-2-one Structure

1-naphthalen-1-...

[2-(benzo[e][1]benzothiol-2-ylmethyl)phenyl]methanol Structure

[2-(benzo[e][1]...

~76%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[e][1]b...

Phthalic anhydride Structure

Phthalic anhydride

~%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[e][1]b...

naphtho[2,1-b]thiophene Structure

naphtho[2,1-b]t...

~%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[e][1]b...

2-(benzo[e][1]benzothiol-2-ylmethyl)benzoic acid Structure

2-(benzo[e][1]b...

~%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[e][1]b...

2-(benzo[e][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[e][1]b...

~%

2-(benzo[e][1]benzothiol-2-ylmethyl)benzaldehyde Structure

2-(benzo[e][1]b...

ethyl naphtho[2,3-b]thiophene-2-carboxylate Structure

ethyl naphtho[2...

~%

2-(2-phenylethenyl)benzo[g][1]benzothiole Structure

2-(2-phenylethe...

4,5-DIHYDRO-2-(ETHOXYCARBONYL)NAPTHO(1,2-B)THIOPENE Structure

4,5-DIHYDRO-2-(...

~%

2-(2-phenylethenyl)benzo[g][1]benzothiole Structure

2-(2-phenylethe...

benzo[g][1]benzothiole-2-carbaldehyde Structure

benzo[g][1]benz...

Diethyl benzylphosphonate Structure

Diethyl benzylp...

~%

2-(2-phenylethenyl)benzo[g][1]benzothiole Structure

2-(2-phenylethe...

Thiophene, 2-(2-phenylethenyl)- Structure

Thiophene, 2-(2...

~73%

naphtho[2,1-b]thiophene Structure

naphtho[2,1-b]t...

Thiophene(SIV) Structure

Phthalic anhydride Structure

Phthalic anhydride

~84%

Benzoic acid,2-(2-thienylcarbonyl)- Structure

Benzoic acid,2-...

2-Mercapto-3-(1-naphthalenyl)propenoic acid Structure

2-Mercapto-3-(1...

~82%

benzo[e][1]benzothiole-2-carboxylic acid Structure

benzo[e][1]benz...

4,5-DIHYDRO-2-(ETHOXYCARBONYL)NAPTHO(1,2-B)THIOPENE Structure

4,5-DIHYDRO-2-(...

~%

benzo[g][1]benzothiole-2-carbaldehyde Structure

benzo[g][1]benz...

ethyl naphtho[2,3-b]thiophene-2-carboxylate Structure

ethyl naphtho[2...

~%

benzo[g][1]benzothiole-2-carbaldehyde Structure

benzo[g][1]benz...

3-methylbenzo[g][1]benzothiole Structure

3-methylbenzo[g...

~76%

benzo[g][1]benzothiole-3-carbaldehyde Structure

benzo[g][1]benz...

1-NAPHTHALENETHIOL Structure

1-NAPHTHALENETHIOL

~%

benzo[g][1]benzothiole-3-carbaldehyde Structure

benzo[g][1]benz...

1-naphthalen-1-ylsulfanylpropan-2-one Structure

1-naphthalen-1-...

~%

benzo[g][1]benzothiole-3-carbaldehyde Structure

benzo[g][1]benz...

1-Aminonaphthalene Structure

1-Aminonaphthalene

~%

benzo[g][1]benzothiole-3-carbaldehyde Structure

benzo[g][1]benz...

ethyl 1-naphthyl xanthate Structure

ethyl 1-naphthy...

~%

benzo[g][1]benzothiole-3-carbaldehyde Structure

benzo[g][1]benz...

ethyl 1-naphthyl xanthate Structure

ethyl 1-naphthy...

~73%

1-NAPHTHALENETHIOL Structure

1-NAPHTHALENETHIOL

2-(hydroxymethyl)naphtho[2,1-b]thiophene Structure

2-(hydroxymethy...

~%

2-(2-phenylethenyl)benzo[e][1]benzothiole Structure

2-(2-phenylethe...

benzo[e][1]benzothiole-2-carboxylic acid Structure

benzo[e][1]benz...

~%

2-(2-phenylethenyl)benzo[e][1]benzothiole Structure

2-(2-phenylethe...

2-Mercapto-3-(1-naphthalenyl)propenoic acid Structure

2-Mercapto-3-(1...

~%

2-(2-phenylethenyl)benzo[e][1]benzothiole Structure

2-(2-phenylethe...

2-naphtho[2,1-b]thiophene-2-carboxaldehyde Structure

2-naphtho[2,1-b...

Diethyl benzylphosphonate Structure

Diethyl benzylp...

~%

2-(2-phenylethenyl)benzo[e][1]benzothiole Structure

2-(2-phenylethe...

Phthalic anhydride Structure

Phthalic anhydride

Naphtho[2,3-b]thiophene Structure

Naphtho[2,3-b]t...

~82%

2-(benzo[f][1]benzothiole-2-carbonyl)benzoic acid Structure

2-(benzo[f][1]b...

3-(2-phenylethenyl)benzo[g][1]benzothiole Structure

3-(2-phenylethe...

~76%

1,2,7,8-Dibenzo-9-thiafluorene Structure

1,2,7,8-Dibenzo...