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

Tetrahedron

Base-and light-assisted synthesis of anthracenes from 3-allylnaphthalene-2-carbaldehydes

CB de Koning, SS Manzini, JP Michael, EM Mmutlane…

Index: De Koning, Charles B.; Manzini, Sunnyboy S.; Michael, Joseph P.; Mmutlane, Edwin M.; Tshabidi, Tefo R.; Van Otterlo, Willem A.L. Tetrahedron, 2005 , vol. 61, # 3 p. 555 - 564

Full Text: HTML

Citation Number: 5

Abstract

The synthesis of substituted anthracenes from naphthalene precursors is described. The key step involved heating ortho-allyl substituted naphthalene-2-carbaldehydes and potassium t- butoxide in DMF with concomitant irradiation from a high pressure mercury lamp to afford anthracenes in yields of 76–98%.

ethyl 4-hydroxy-5,8-dimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

(3-but-3-en-2-yl-4,5,8-trimethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

(4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,6,8-tetram...

~67%

4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,6,8-tetrame...

2,4,5-Trimethoxybenzaldehyde Structure

2,4,5-Trimethox...

~%

4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,6,8-tetrame...

(E)-3-ethoxycarbonyl-4-(2,4,5-trimethoxyphenyl)but-3-enoic acid Structure

(E)-3-ethoxycar...

~%

4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,6,8-tetrame...

ethyl 4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,6,8-tetrame...

ethyl 5,6,8-trimethoxy-4-(prop-2-enyloxy)-2-naphthoate Structure

ethyl 5,6,8-tri...

~%

4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,6,8-tetrame...

ethyl 4,5,6,8-tetramethoxy-3-(prop-2-enyl)-2-naphthoate Structure

ethyl 4,5,6,8-t...

~%

4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,6,8-tetrame...

(4,5,8-trimethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,8-trimetho...

~76%

4,5,8-trimethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,8-trimethox...

Ethyl 4-acetoxy-5,8-dimethoxy-2-naphthoate Structure

Ethyl 4-acetoxy...

~%

4,5,8-trimethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,8-trimethox...

ethyl 4-hydroxy-5,8-dimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

4,5,8-trimethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,8-trimethox...

ethyl 5,8-dimethoxy-4-(prop-2-enyloxy)-2-naphthoate Structure

ethyl 5,8-dimet...

~%

4,5,8-trimethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,8-trimethox...

ethyl 4,5,8-trimethoxy-3-(prop-2-enyl)-2-naphthoate Structure

ethyl 4,5,8-tri...

~%

4,5,8-trimethoxy-3-prop-2-enylnaphthalene-2-carbaldehyde Structure

4,5,8-trimethox...

ethyl 4,5,6,8-tetramethoxy-3-(prop-2-enyl)-2-naphthoate Structure

ethyl 4,5,6,8-t...

~89%

(4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,6,8-tetram...

2,4,5-Trimethoxybenzaldehyde Structure

2,4,5-Trimethox...

~%

(4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,6,8-tetram...

(E)-3-ethoxycarbonyl-4-(2,4,5-trimethoxyphenyl)but-3-enoic acid Structure

(E)-3-ethoxycar...

~%

(4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,6,8-tetram...

ethyl 4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

(4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,6,8-tetram...

ethyl 5,6,8-trimethoxy-4-(prop-2-enyloxy)-2-naphthoate Structure

ethyl 5,6,8-tri...

~%

(4,5,6,8-tetramethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,6,8-tetram...

2,4,5-Trimethoxybenzaldehyde Structure

2,4,5-Trimethox...

~%

ethyl 4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

(E)-3-ethoxycarbonyl-4-(2,4,5-trimethoxyphenyl)but-3-enoic acid Structure

(E)-3-ethoxycar...

~%

ethyl 4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

ethyl 4,5,6,8-tetramethoxy-3-(2-methylprop-2-enyl)-2-naphthoate Structure

ethyl 4,5,6,8-t...

~94%

[4,5,6,8-tetramethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,6,8-tetram...

2,4,5-Trimethoxybenzaldehyde Structure

2,4,5-Trimethox...

~%

[4,5,6,8-tetramethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,6,8-tetram...

(E)-3-ethoxycarbonyl-4-(2,4,5-trimethoxyphenyl)but-3-enoic acid Structure

(E)-3-ethoxycar...

~%

[4,5,6,8-tetramethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,6,8-tetram...

ethyl 4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

[4,5,6,8-tetramethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,6,8-tetram...

ethyl 5,6,8-trimethoxy-4-(2-methylprop-2-enyloxy)-2-naphthoate Structure

ethyl 5,6,8-tri...

~%

[4,5,6,8-tetramethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,6,8-tetram...

ethyl 4,5,6,8-tetramethoxy-3-(1-methylprop-2-enyl)-2-naphthoate Structure

ethyl 4,5,6,8-t...

~85%

(3-but-3-en-2-yl-4,5,6,8-tetramethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

2,4,5-Trimethoxybenzaldehyde Structure

2,4,5-Trimethox...

~%

(3-but-3-en-2-yl-4,5,6,8-tetramethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

(E)-3-ethoxycarbonyl-4-(2,4,5-trimethoxyphenyl)but-3-enoic acid Structure

(E)-3-ethoxycar...

~%

(3-but-3-en-2-yl-4,5,6,8-tetramethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

ethyl 4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

(3-but-3-en-2-yl-4,5,6,8-tetramethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

ethyl 5,6,8-trimethoxy-4-(but-2-enyloxy)-2-naphthoate Structure

ethyl 5,6,8-tri...

~%

(3-but-3-en-2-yl-4,5,6,8-tetramethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

ethyl 4,5,8-trimethoxy-3-(prop-2-enyl)-2-naphthoate Structure

ethyl 4,5,8-tri...

~90%

(4,5,8-trimethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,8-trimetho...

Ethyl 4-acetoxy-5,8-dimethoxy-2-naphthoate Structure

Ethyl 4-acetoxy...

~%

(4,5,8-trimethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,8-trimetho...

ethyl 4-hydroxy-5,8-dimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

(4,5,8-trimethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,8-trimetho...

ethyl 5,8-dimethoxy-4-(prop-2-enyloxy)-2-naphthoate Structure

ethyl 5,8-dimet...

~%

(4,5,8-trimethoxy-3-prop-2-enylnaphthalen-2-yl)methanol Structure

(4,5,8-trimetho...

ethyl 4,5,8-trimethoxy-3-(2-methylprop-2-enyl)-2-naphthoate Structure

ethyl 4,5,8-tri...

~88%

[4,5,8-trimethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,8-trimetho...

Ethyl 4-acetoxy-5,8-dimethoxy-2-naphthoate Structure

Ethyl 4-acetoxy...

~%

[4,5,8-trimethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,8-trimetho...

ethyl 4-hydroxy-5,8-dimethoxynaphthalene-2-carboxylate Structure

ethyl 4-hydroxy...

~%

[4,5,8-trimethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,8-trimetho...

ethyl 5,8-dimethoxy-4-(2-methylprop-2-enyloxy)-2-naphthoate Structure

ethyl 5,8-dimet...

~%

[4,5,8-trimethoxy-3-(2-methylprop-2-enyl)naphthalen-2-yl]methanol Structure

[4,5,8-trimetho...

ethyl 4,5,8-trimethoxy-3-(1-methylprop-2-enyl)-2-naphthoate Structure

ethyl 4,5,8-tri...

~86%

(3-but-3-en-2-yl-4,5,8-trimethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...

Ethyl 4-acetoxy-5,8-dimethoxy-2-naphthoate Structure

Ethyl 4-acetoxy...

~%

(3-but-3-en-2-yl-4,5,8-trimethoxynaphthalen-2-yl)methanol Structure

(3-but-3-en-2-y...