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

Synthesis of isocoumarin derivatives via the copper-catalyzed tandem sequential cyclization of 2-halo-N-phenyl benzamides and acyclic 1, 3-diketones

…, CC Wang, DK Barange, CW Kuo, PM Lei…

Index: Kavala, Veerababurao; Wang, Cheng-Chuan; Barange, Deepak Kumar; Kuo, Chun-Wei; Lei, Po-Min; Yao, Ching-Fa Journal of Organic Chemistry, 2012 , vol. 77, # 11 p. 5022 - 5029

Full Text: HTML

Citation Number: 51

Abstract

A facile and rapid synthesis of isocoumarin derivatives using a copper-catalyzed tandem C– C/C–O coupling strategy from readily available substrates is described. The reactions of a wide range of 2-iodo-N-phenyl benzamides and acyclic diketones as starting materials were investigated.

Bis(4-methoxybenzoyl)methane Structure

Bis(4-methoxybe...

Benodanil Structure

~81%

3-(4-methoxyphenyl)isochromen-1-one Structure

3-(4-methoxyphe...

4-methoxy-N-phenyl-benzamide Structure

4-methoxy-N-phe...

Benodanil Structure

1,3-Diphenylpropane-1,3-dione Structure

1,3-Diphenylpro...

~64%

Benzanilide Structure

3-phenylisochromen-1-one Structure

3-phenylisochro...

Benodanil Structure

1-Phenylbutane-1,3-dione Structure

1-Phenylbutane-...

~56%

Benzanilide Structure

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Detail

6-iodo-2,3-dimethoxy-N-phenylbenzamide Structure

6-iodo-2,3-dime...

2,4-Pentandione Structure

2,4-Pentandione

~0%

7,8-dimethoxy-3-methyl-1H-isochromen-1-one Structure

7,8-dimethoxy-3...

Acetanilide Structure

6-iodo-N-phenylbenzo[d][1,3]dioxole-5-carboxamide Structure

6-iodo-N-phenyl...

2,4-Pentandione Structure

2,4-Pentandione

~0%

7-methyl-[1,3]dioxolo[4,5-g]isochromen-5-one Structure

7-methyl-[1,3]d...

Acetanilide Structure

4-fluoro-2-iodo-N-phenylbenzamide Structure

4-fluoro-2-iodo...

2,4-Pentandione Structure

2,4-Pentandione

~0%

6-fluoro-3-methyl-1H-isochromen-1-one Structure

6-fluoro-3-meth...

Acetanilide Structure

4-chloro-2-iodo-N-phenylbenzamide Structure

4-chloro-2-iodo...

2,4-Pentandione Structure

2,4-Pentandione

~0%

6-chloro-3-methylisochromen-1-one Structure

6-chloro-3-meth...

Acetanilide Structure

N/A Structure

2,4-Pentandione Structure

2,4-Pentandione

~0%

3,7-dimethyl-1H-isochromen-1-one Structure

3,7-dimethyl-1H...

Acetanilide Structure

6-iodo-N-phenylbenzo[d][1,3]dioxole-5-carboxamide Structure

6-iodo-N-phenyl...

2,4-Pentandione Structure

2,4-Pentandione

~72%

7-methyl-[1,3]dioxolo[4,5-g]isochromen-5-one Structure

7-methyl-[1,3]d...

Acetanilide Structure

2-iodo-4,5-dimethoxy-N-phenylbenzamide Structure

2-iodo-4,5-dime...

2,4-Pentandione Structure

2,4-Pentandione

~0%

6,7-dimethoxy-3-methyl-1H-isochromen-1-one Structure

6,7-dimethoxy-3...

Acetanilide Structure

3,5-dibromo-2-iodo-N-phenylbenzamide Structure

3,5-dibromo-2-i...

2,4-Pentandione Structure

2,4-Pentandione

~0%

N/A Structure

Acetanilide Structure

Structure

2,4-Pentandione Structure

2,4-Pentandione

~0%

2-methyl-4H-naphtho[2,1-c]pyran-4-one Structure

2-methyl-4H-nap...

Acetanilide Structure

2-iodo-5-methoxy-N-phenylbenzamide Structure

2-iodo-5-methox...

2,4-Pentandione Structure

2,4-Pentandione

~0%

N/A Structure

Acetanilide Structure

Benodanil Structure

2,4-Pentandione Structure

2,4-Pentandione

~0%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Acetanilide Structure

Benzamide,2-chloro-N-phenyl- Structure

Benzamide,2-chl...

2,4-Pentandione Structure

2,4-Pentandione

~0%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Acetanilide Structure

2-bromo-N-phenylbenzamide Structure

2-bromo-N-pheny...

2,4-Pentandione Structure

2,4-Pentandione

~0%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Acetanilide Structure

Benodanil Structure

2,4-Pentandione Structure

2,4-Pentandione

~90%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Acetanilide Structure

Benzamide,2-chloro-N-phenyl- Structure

Benzamide,2-chl...

2,4-Pentandione Structure

2,4-Pentandione

~82%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Acetanilide Structure

2-bromo-N-phenylbenzamide Structure

2-bromo-N-pheny...

2,4-Pentandione Structure

2,4-Pentandione

~80%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Acetanilide Structure

Benodanil Structure

1-Phenylbutane-1,3-dione Structure

1-Phenylbutane-...

~9%

Benzanilide Structure

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

Detail

2-iodo-N-methylbenzamide Structure

2-iodo-N-methyl...

2,4-Pentandione Structure

2,4-Pentandione

~69%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

2-iodo-N-benzylbenzamide Structure

2-iodo-N-benzyl...

2,4-Pentandione Structure

2,4-Pentandione

~75%

3-METHYL-ISOCHROMEN-1-ONE Structure

3-METHYL-ISOCHR...

4-chloro-2-iodo-N-phenylbenzamide Structure

4-chloro-2-iodo...

2,4-Pentandione Structure

2,4-Pentandione

~72%

6-chloro-3-methylisochromen-1-one Structure

6-chloro-3-meth...

Acetanilide Structure

1,3-Propanedione, 1,3-bis(4-methylphenyl)- Structure

1,3-Propanedion...

Benodanil Structure

~63%

3-(4-methylphenyl)isochromen-1-one Structure

3-(4-methylphen...

4-METHYLBENZANILIDE Structure

4-METHYLBENZANILIDE

1,3-Propanedione, 1,3-bis(4-methylphenyl)- Structure

1,3-Propanedion...

3,5-dibromo-2-iodo-N-phenylbenzamide Structure

3,5-dibromo-2-i...

~0%

4-METHYLBENZANILIDE Structure

4-METHYLBENZANILIDE

5,7-dibromo-3-(p-tolyl)-1H-isochromen-1-one Structure

5,7-dibromo-3-(...

1,3-Propanedione, 1,3-bis(4-methylphenyl)- Structure

1,3-Propanedion...

Benodanil Structure

~0%

3-(4-methylphenyl)isochromen-1-one Structure

3-(4-methylphen...

4-METHYLBENZANILIDE Structure

4-METHYLBENZANILIDE

Gold-catalyzed C–S bond formation from thiols

[Jean, Mickael; Renault, Jacques; van de Weghe, Pierre; Asao, Naoki Tetrahedron Letters, 2010 , vol. 51, # 2 p. 378 - 381]

Gold-catalyzed C–S bond formation from thiols

[Jean, Mickael; Renault, Jacques; van de Weghe, Pierre; Asao, Naoki Tetrahedron Letters, 2010 , vol. 51, # 2 p. 378 - 381]

Gold-catalyzed C–S bond formation from thiols

[Jean, Mickael; Renault, Jacques; van de Weghe, Pierre; Asao, Naoki Tetrahedron Letters, 2010 , vol. 51, # 2 p. 378 - 381]

Gold-catalyzed C–S bond formation from thiols

[Jean, Mickael; Renault, Jacques; van de Weghe, Pierre; Asao, Naoki Tetrahedron Letters, 2010 , vol. 51, # 2 p. 378 - 381]

Gold-catalyzed C–S bond formation from thiols

[Jean, Mickael; Renault, Jacques; van de Weghe, Pierre; Asao, Naoki Tetrahedron Letters, 2010 , vol. 51, # 2 p. 378 - 381]