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Helvetica chimica acta

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

P Wessig, G Müller, R Herre, A Kühn

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

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被引用次数: 18

摘要

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结构式

N-methoxy-N-met...

1-乙炔基萘结构式

~68%

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

4-naphthalen-1-...

碘苯结构式

~%

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

4-naphthalen-1-...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

4-naphthalen-1-...

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

ethyl [(3-pheny...

~%

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

4-naphthalen-1-...

α-碘萘结构式

~%

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

1-(3-naphthalen...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

1-(3-naphthalen...

ethyl 2-(3-naphthalen-1-ylprop-2-ynoxy)acetate结构式

ethyl 2-(3-naph...

~%

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

1-(3-naphthalen...

4-氟碘苯结构式

丙炔醇结构式

~99%

3-(4-氟苯基)-2-丙炔-1-醇结构式

3-(4-氟苯基)-2-丙炔-1-醇

2,4,6-三甲基碘苯结构式

2,4,6-三甲基碘苯

丙炔醇结构式

~49%

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

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

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

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

溴乙酸结构式

~44%

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

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

2,4,6-三甲基碘苯结构式

2,4,6-三甲基碘苯

~%

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

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

3-methyl-1-phenyl-1-propyne-3-ol结构式

3-methyl-1-phen...

溴乙酸结构式

~78%

2-(4-phenylbut-3-yn-2-yloxy)acetic acid结构式

2-(4-phenylbut-...

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

N-methyl-N-meth...

苯乙炔结构式

~79%

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

1-(3-naphthalen...

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

1-乙炔基-3,5-二甲苯结构式

1-乙炔基-3,5-二甲苯

~51%

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

4-(3,5-dimethyl...

碘苯结构式

~%

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

4-(3,5-dimethyl...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

4-(3,5-dimethyl...

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

ethyl [(3-pheny...

~%

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

4-(3,5-dimethyl...

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

N-methyl-N-meth...

苯乙炔结构式

~36%

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

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

2,4,6-三甲基碘苯结构式

2,4,6-三甲基碘苯

~%

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

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

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

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

~%

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

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

α-碘萘结构式

~%

4-naphthalen-1-ylbut-3-yn-2-one结构式

4-naphthalen-1-...

ethyl 2-(3-naphthalen-1-ylprop-2-ynoxy)acetate结构式

ethyl 2-(3-naph...

~%

4-naphthalen-1-ylbut-3-yn-2-one结构式

4-naphthalen-1-...

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

N-methyl-N-meth...

~%

4-naphthalen-1-ylbut-3-yn-2-one结构式

4-naphthalen-1-...

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

1-(3-naphthalen...

~%

苯丙炔醛结构式

4-naphthalen-1-ylbut-3-yn-2-one结构式

4-naphthalen-1-...

isopropyl phenylethynyl carbinol结构式

isopropyl pheny...

溴乙酸结构式

~65%

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

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

ethyl 2-(1,3-diphenylprop-2-ynoxy)acetate结构式

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

~%

2-(1,3-diphenylprop-2-ynoxy)acetic acid结构式

2-(1,3-diphenyl...

1,3-二苯基-2-丙炔-1-醇结构式

1,3-二苯基-2-丙炔-1-醇

~%

2-(1,3-diphenylprop-2-ynoxy)acetic acid结构式

2-(1,3-diphenyl...

2-(1,3-diphenylprop-2-ynoxy)acetic acid结构式

2-(1,3-diphenyl...

二甲羟胺盐酸盐结构式

二甲羟胺盐酸盐

~81%

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

2-(1,3-diphenyl...

ethyl 2-(1,3-diphenylprop-2-ynoxy)acetate结构式

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

~%

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

2-(1,3-diphenyl...

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

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

~%

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

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

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

2-乙炔基-1,3,5-三甲基苯结构式

2-乙炔基-1,3,5-三甲基苯

~65%

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

1-(3-phenylprop...

碘苯结构式

~%

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

1-(3-phenylprop...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

1-(3-phenylprop...

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

ethyl [(3-pheny...

~%

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

1-(3-phenylprop...

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

N-methyl-N-meth...

苯乙炔结构式

~69%

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

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

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

苯乙炔结构式

~81%

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

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

碘苯结构式

~%

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

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

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

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

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

ethyl [(3-pheny...

~%

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

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

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

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

苯乙炔结构式

~61%

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

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

对氯碘苯结构式

~%

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

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

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

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

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

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

~%

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

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

1,3-二苯基-2-丙炔-1-醇结构式

1,3-二苯基-2-丙炔-1-醇

溴乙酸乙酯结构式

溴乙酸乙酯

~65%

ethyl 2-(1,3-diphenylprop-2-ynoxy)acetate结构式

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

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

N-methyl-N-meth...

苯乙炔结构式

~69%

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

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

对碘甲苯结构式

~%

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

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

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

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

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

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

~%

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

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

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

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

苯乙炔结构式

~65%

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

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

4-氟碘苯结构式

~%

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

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

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

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

~%

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

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

3-(4-氟苯基)-2-丙炔-1-醇结构式

3-(4-氟苯基)-2-丙炔-1-醇

~%

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

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

对氯碘苯结构式

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~67%

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

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

对碘甲苯结构式

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~66%

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

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

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

1-氯-4-乙炔基苯结构式

1-氯-4-乙炔基苯

~68%

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

4-(4-chlorophen...

碘苯结构式

~%

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

4-(4-chlorophen...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

4-(4-chlorophen...

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

ethyl [(3-pheny...

~%

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

4-(4-chlorophen...

4-氟碘苯结构式

~%

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

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

溴乙酸乙酯结构式

溴乙酸乙酯

3-(4-氟苯基)-2-丙炔-1-醇结构式

3-(4-氟苯基)-2-丙炔-1-醇

~%

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

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

α-碘萘结构式

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~47%

ethyl 2-(3-naphthalen-1-ylprop-2-ynoxy)acetate结构式

ethyl 2-(3-naph...

碘苯结构式

~%

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

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

ethyl [(3-pheny...

~%

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

4-氟苯乙炔结构式

~57%

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

4-(4-fluorophen...

碘苯结构式

~%

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

4-(4-fluorophen...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

4-(4-fluorophen...

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

ethyl [(3-pheny...

~%

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

4-(4-fluorophen...

N-methoxy-N-methyl-2-(3-phenylprop-2-ynoxy)acetamide结构式

N-methoxy-N-met...

4-乙炔基甲苯结构式

4-乙炔基甲苯

~64%

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

4-(4-methylphen...

碘苯结构式

~%

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

4-(4-methylphen...

ethyl 2-prop-2-ynoxyacetate结构式

ethyl 2-prop-2-...

~%

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

4-(4-methylphen...

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

ethyl [(3-pheny...

~%

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

4-(4-methylphen...