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

Helvetica chimica acta

Synthesis of Benzo [g] isochromenes through Photo??Dehydro??Diels–Alder Reaction

P Wessig, G Müller, R Herre, A Kühn

Index: Wessig, Pablo; Mueller, Gunnar; Herre, Robert; Kuehn, Andreas Helvetica Chimica Acta, 2006 , vol. 89, # 11 p. 2694 - 2719

Full Text: HTML

Citation Number: 18

Abstract

Abstract The Photo-Dehydro-Diels–Alder (PDDA) reaction is shown to be a versatile method for the preparation of highly functionalized naphthalenes. Thus, ketones 1 could be cyclized to the 1H-benzo [g] isochromen-4-(3H)-ones 11 and 12, mostly in good yields. The influence of various substituents on the regioselectivity of the reaction was investigated, and the mechanism is discussed based on theoretical calculations.

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

~68%

4-naphthalen-1-yl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-naphthalen-1-...

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Iodobenzene Structure

~%

4-naphthalen-1-yl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-naphthalen-1-...

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ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

4-naphthalen-1-yl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-naphthalen-1-...

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ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

4-naphthalen-1-yl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-naphthalen-1-...

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1-Iodonaphthalene Structure

1-Iodonaphthalene

~%

1-(3-naphthalen-1-ylprop-2-ynoxy)-4-phenylbut-3-yn-2-one Structure

1-(3-naphthalen...

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ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

1-(3-naphthalen-1-ylprop-2-ynoxy)-4-phenylbut-3-yn-2-one Structure

1-(3-naphthalen...

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ethyl 2-(3-naphthalen-1-ylprop-2-ynoxy)acetate Structure

ethyl 2-(3-naph...

~%

1-(3-naphthalen-1-ylprop-2-ynoxy)-4-phenylbut-3-yn-2-one Structure

1-(3-naphthalen...

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4-Fluoroiodobenzene Structure

4-Fluoroiodobenzene

Propargyl alcohol Structure

Propargyl alcohol

~99%

3-(4-Fluorophenyl)-2-propyn-1-ol Structure

3-(4-Fluorophen...

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Iodo-2,4,6-trimethylbenzene Structure

Iodo-2,4,6-trim...

Propargyl alcohol Structure

Propargyl alcohol

~49%

3-(2,4,6-trimethylphenyl)prop-2-yn-1-ol Structure

3-(2,4,6-trimet...

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3-(2,4,6-trimethylphenyl)prop-2-yn-1-ol Structure

3-(2,4,6-trimet...

Bromoacetic acid Structure

Bromoacetic acid

~44%

2-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]acetic acid Structure

2-[3-(2,4,6-tri...

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Iodo-2,4,6-trimethylbenzene Structure

Iodo-2,4,6-trim...

~%

2-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]acetic acid Structure

2-[3-(2,4,6-tri...

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3-methyl-1-phenyl-1-propyne-3-ol Structure

3-methyl-1-phen...

Bromoacetic acid Structure

Bromoacetic acid

~78%

2-(4-phenylbut-3-yn-2-yloxy)acetic acid Structure

2-(4-phenylbut-...

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N-methyl-N-methoxy-2-{[3-(naphthalene-1-yl)prop-2-yn-1-yl]oxy}acetamide Structure

N-methyl-N-meth...

Phenylacetylene Structure

Phenylacetylene

~79%

1-(3-naphthalen-1-ylprop-2-ynoxy)-4-phenylbut-3-yn-2-one Structure

1-(3-naphthalen...

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N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

1-ETHYNYL-3,5-DIMETHYL-BENZENE Structure

1-ETHYNYL-3,5-D...

~51%

4-(3,5-dimethylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(3,5-dimethyl...

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Iodobenzene Structure

~%

4-(3,5-dimethylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(3,5-dimethyl...

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ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

4-(3,5-dimethylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(3,5-dimethyl...

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ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

4-(3,5-dimethylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(3,5-dimethyl...

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N-methyl-N-methoxy-2-{[3-(2,4,6-trimethylphenyl)prop-2-yn-1-yl]oxy}acetamide Structure

N-methyl-N-meth...

Phenylacetylene Structure

Phenylacetylene

~36%

4-phenyl-1-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]but-3-yn-2-one Structure

4-phenyl-1-[3-(...

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Iodo-2,4,6-trimethylbenzene Structure

Iodo-2,4,6-trim...

~%

4-phenyl-1-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]but-3-yn-2-one Structure

4-phenyl-1-[3-(...

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2-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]acetic acid Structure

2-[3-(2,4,6-tri...

~%

4-phenyl-1-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]but-3-yn-2-one Structure

4-phenyl-1-[3-(...

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1-Iodonaphthalene Structure

1-Iodonaphthalene

~%

4-naphthalen-1-ylbut-3-yn-2-one Structure

4-naphthalen-1-...

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ethyl 2-(3-naphthalen-1-ylprop-2-ynoxy)acetate Structure

ethyl 2-(3-naph...

~%

4-naphthalen-1-ylbut-3-yn-2-one Structure

4-naphthalen-1-...

Learn More

N-methyl-N-methoxy-2-{[3-(naphthalene-1-yl)prop-2-yn-1-yl]oxy}acetamide Structure

N-methyl-N-meth...

~%

4-naphthalen-1-ylbut-3-yn-2-one Structure

4-naphthalen-1-...

Learn More

1-(3-naphthalen-1-ylprop-2-ynoxy)-4-phenylbut-3-yn-2-one Structure

1-(3-naphthalen...

~%

phenylpropynal Structure

4-naphthalen-1-ylbut-3-yn-2-one Structure

4-naphthalen-1-...

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isopropyl phenylethynyl carbinol Structure

isopropyl pheny...

Bromoacetic acid Structure

Bromoacetic acid

~65%

2-(4-methyl-1-phenylpent-1-yn-3-yl)oxyacetic acid Structure

2-(4-methyl-1-p...

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ethyl 2-(1,3-diphenylprop-2-ynoxy)acetate Structure

ethyl 2-(1,3-di...

~%

2-(1,3-diphenylprop-2-ynoxy)acetic acid Structure

2-(1,3-diphenyl...

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Benzenemethanol, a-(2-phenylethynyl) Structure

Benzenemethanol...

~%

2-(1,3-diphenylprop-2-ynoxy)acetic acid Structure

2-(1,3-diphenyl...

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2-(1,3-diphenylprop-2-ynoxy)acetic acid Structure

2-(1,3-diphenyl...

N,O-Dimethylhydroxylamine hydrochloride Structure

N,O-Dimethylhyd...

~81%

2-(1,3-diphenylprop-2-ynoxy)-N-methoxy-N-methylacetamide Structure

2-(1,3-diphenyl...

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ethyl 2-(1,3-diphenylprop-2-ynoxy)acetate Structure

ethyl 2-(1,3-di...

~%

2-(1,3-diphenylprop-2-ynoxy)-N-methoxy-N-methylacetamide Structure

2-(1,3-diphenyl...

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3-(2,4,6-trimethylphenyl)prop-2-yn-1-ol Structure

3-(2,4,6-trimet...

~%

4-phenyl-1-[3-(2,4,6-trimethylphenyl)prop-2-ynoxy]but-3-yn-2-one Structure

4-phenyl-1-[3-(...

Learn More

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

1-Ethynyl-2,4,6-trimethylbenzene Structure

1-Ethynyl-2,4,6...

~65%

1-(3-phenylprop-2-ynoxy)-4-(2,4,6-trimethylphenyl)but-3-yn-2-one Structure

1-(3-phenylprop...

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Iodobenzene Structure

~%

1-(3-phenylprop-2-ynoxy)-4-(2,4,6-trimethylphenyl)but-3-yn-2-one Structure

1-(3-phenylprop...

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ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

1-(3-phenylprop-2-ynoxy)-4-(2,4,6-trimethylphenyl)but-3-yn-2-one Structure

1-(3-phenylprop...

Learn More

ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

1-(3-phenylprop-2-ynoxy)-4-(2,4,6-trimethylphenyl)but-3-yn-2-one Structure

1-(3-phenylprop...

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N-methyl-N-methoxy-2-[(1-methyl-3-phenylprop-2-yn-1-yl)oxy]acetamide Structure

N-methyl-N-meth...

Phenylacetylene Structure

Phenylacetylene

~69%

4-phenyl-1-(4-phenylbut-3-yn-2-yloxy)but-3-yn-2-one Structure

4-phenyl-1-(4-p...

Learn More

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

Phenylacetylene Structure

Phenylacetylene

~81%

4-phenyl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-phenyl-1-(3-p...

Learn More

Iodobenzene Structure

~%

4-phenyl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-phenyl-1-(3-p...

Learn More

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

4-phenyl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-phenyl-1-(3-p...

Learn More

ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

4-phenyl-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-phenyl-1-(3-p...

Learn More

2-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-N-methyl-N-methoxyacetamide Structure

2-{[3-(4-chloro...

Phenylacetylene Structure

Phenylacetylene

~61%

1-[3-(4-chlorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-chlorop...

Learn More

1-Chloro-4-iodobenzene Structure

1-Chloro-4-iodo...

~%

1-[3-(4-chlorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-chlorop...

Learn More

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

1-[3-(4-chlorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-chlorop...

Learn More

ethyl 2-[3-(4-chlorophenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-c...

~%

1-[3-(4-chlorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-chlorop...

Learn More

Benzenemethanol, a-(2-phenylethynyl) Structure

Benzenemethanol...

ethyl 2-bromoacetate Structure

ethyl 2-bromoacetate

~65%

ethyl 2-(1,3-diphenylprop-2-ynoxy)acetate Structure

ethyl 2-(1,3-di...

Learn More

N-methyl-N-methoxy-2-{[3-(4-methylphenyl)prop-2-yn-1-yl]oxy}acetamide Structure

N-methyl-N-meth...

Phenylacetylene Structure

Phenylacetylene

~69%

1-[3-(4-methylphenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-methylp...

Learn More

4-Iodotoluene Structure

~%

1-[3-(4-methylphenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-methylp...

Learn More

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

1-[3-(4-methylphenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-methylp...

Learn More

ethyl 2-[3-(4-methylphenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-m...

~%

1-[3-(4-methylphenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-methylp...

Learn More

2-{[3-(4-fluorophenyl)prop-2-yn-1-yl]oxy}-N-methyl-N-methoxyacetamide Structure

2-{[3-(4-fluoro...

Phenylacetylene Structure

Phenylacetylene

~65%

1-[3-(4-fluorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-fluorop...

Learn More

4-Fluoroiodobenzene Structure

4-Fluoroiodobenzene

~%

1-[3-(4-fluorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-fluorop...

Learn More

ethyl 2-[3-(4-fluorophenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-f...

~%

1-[3-(4-fluorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-fluorop...

Learn More

3-(4-Fluorophenyl)-2-propyn-1-ol Structure

3-(4-Fluorophen...

~%

1-[3-(4-fluorophenyl)prop-2-ynoxy]-4-phenylbut-3-yn-2-one Structure

1-[3-(4-fluorop...

Learn More

1-Chloro-4-iodobenzene Structure

1-Chloro-4-iodo...

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~67%

ethyl 2-[3-(4-chlorophenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-c...

Learn More

4-Iodotoluene Structure

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~66%

ethyl 2-[3-(4-methylphenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-m...

Learn More

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

4-Chlorophenylacetylene Structure

4-Chlorophenyla...

~68%

4-(4-chlorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-chlorophen...

Learn More

Iodobenzene Structure

~%

4-(4-chlorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-chlorophen...

Learn More

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

4-(4-chlorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-chlorophen...

Learn More

ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

4-(4-chlorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-chlorophen...

Learn More

4-Fluoroiodobenzene Structure

4-Fluoroiodobenzene

~%

ethyl 2-[3-(4-fluorophenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-f...

Learn More

ethyl 2-bromoacetate Structure

ethyl 2-bromoacetate

3-(4-Fluorophenyl)-2-propyn-1-ol Structure

3-(4-Fluorophen...

~%

ethyl 2-[3-(4-fluorophenyl)prop-2-ynoxy]acetate Structure

ethyl 2-[3-(4-f...

Learn More

1-Iodonaphthalene Structure

1-Iodonaphthalene

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~47%

ethyl 2-(3-naphthalen-1-ylprop-2-ynoxy)acetate Structure

ethyl 2-(3-naph...

Learn More

Iodobenzene Structure

~%

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

Learn More

ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

Learn More

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

4-Fluorophenylacetylene Structure

4-Fluorophenyla...

~57%

4-(4-fluorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-fluorophen...

Learn More

Iodobenzene Structure

~%

4-(4-fluorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-fluorophen...

Learn More

ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

4-(4-fluorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-fluorophen...

Learn More

ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

4-(4-fluorophenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-fluorophen...

Learn More

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide Structure

N-methoxy-N-met...

4-Ethynyltoluene Structure

4-Ethynyltoluene

~64%

4-(4-methylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-methylphen...

Learn More

Iodobenzene Structure

~%

4-(4-methylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-methylphen...

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ethyl 2-prop-2-ynoxyacetate Structure

ethyl 2-prop-2-...

~%

4-(4-methylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-methylphen...

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ethyl [(3-phenylprop-2-yn-1-yl)oxy]acetate Structure

ethyl [(3-pheny...

~%

4-(4-methylphenyl)-1-(3-phenylprop-2-ynoxy)but-3-yn-2-one Structure

4-(4-methylphen...

Learn More