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

Expeditious Approach to Pyrrolophenanthridones, Phenanthridines, and Benzo [c] phenanthridines via Organocatalytic Direct Biaryl-Coupling Promoted by Potassium …

…, S Mishra, BN Kakde, D Dey, A Bisai

Index: De, Subhadip; Mishra, Sourabh; Kakde, Badrinath N.; Dey, Dhananjay; Bisai, Alakesh Journal of Organic Chemistry, 2013 , vol. 78, # 16 p. 7823 - 7844

Full Text: HTML

Citation Number: 39

Abstract

A methodology involving a “transition metal-free” intramolecular biaryl-coupling of o-halo-N- arylbenzylamines has been developed in the presence of potassium tert-butoxide and an organic molecule as catalyst. The reaction appears to proceed through KO t Bu-promoted intramolecular homolytic aromatic substitution (HAS). Interestingly, this biaryl coupling also works in the presence of potassium tert-butoxide as sole promoter. On extending our ...

2-Bromo-4,5-dimethoxybenzaldehyde Structure

2-Bromo-4,5-dim...

Structure

~%

1-(2-bromo-4,5-dimethoxyphenyl)-N-phenylmethanimine Structure

1-(2-bromo-4,5-...

veratraldehyde Structure

~%

1-Oxo-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene oxime Structure

1-Oxo-6,7-dimet...

N/A Structure

~%

1-Oxo-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene oxime Structure

1-Oxo-6,7-dimet...

N-(2-bromo-4,5-dimethoxybenzyl)-N-methylnaphtho[2,3-d][1,3]dioxol-5-amine Structure

N-(2-bromo-4,5-...

~66%

[1,3]Benzodioxolo[5,6-c]phenanthridine,12,13-dihydro-2,3-dimethoxy-12-methyl- Structure

[1,3]Benzodioxo...

Naphtho[2,3-d][1,3]dioxol-5-amine Structure

Naphtho[2,3-d][...

~%

[1,3]Benzodioxolo[5,6-c]phenanthridine,12,13-dihydro-2,3-dimethoxy-12-methyl- Structure

[1,3]Benzodioxo...

N/A Structure

~%

[1,3]Benzodioxolo[5,6-c]phenanthridine,12,13-dihydro-2,3-dimethoxy-12-methyl- Structure

[1,3]Benzodioxo...

Methanone,(2-bromo-4,5-dimethoxyphenyl)(3,4-dihydro-1(2H)-quinolinyl)- Structure

Methanone,(2-br...

~62%

5,6-dihydro-10,11-dimethoxy-4H,8H-pyrido<3,2,1-de>phenanthridin-8-one Structure

5,6-dihydro-10,...

6-iodo-3,4-dimethoxy-N-tetrahydroquinolyl-benzamide Structure

6-iodo-3,4-dime...

~52%

5,6-dihydro-10,11-dimethoxy-4H,8H-pyrido<3,2,1-de>phenanthridin-8-one Structure

5,6-dihydro-10,...

1-Aminonaphthalene Structure

1-Aminonaphthalene

~%

N-(1-Naphtyl)benzenemethaneamine Structure

N-(1-Naphtyl)be...

Benzamide,N-1-naphthalenyl- Structure

Benzamide,N-1-n...

~%

N-(1-Naphtyl)benzenemethaneamine Structure

N-(1-Naphtyl)be...

Methanone,(6-bromo-1,3-benzodioxol-5-yl)(2,3-dihydro-1H-indol-1-yl)- Structure

Methanone,(6-br...

~50%

Anhydrolycorinone Structure

Anhydrolycorinone

N-(6-bromo-2,3-dimethoxybenzyl)-N-methyl-6,7-methylenedioxy-1-naphthylamine Structure

N-(6-bromo-2,3-...

~64%

Dihydrochelerythrine Structure

Dihydrochelerythrine

Naphtho[2,3-d][1,3]dioxol-5-amine Structure

Naphtho[2,3-d][...

~%

Dihydrochelerythrine Structure

Dihydrochelerythrine

N/A Structure

~%

Dihydrochelerythrine Structure

Dihydrochelerythrine

N-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)benzenamine Structure

N-((6-bromobenz...

~68%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...

N/A Structure

~75%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...

N/A Structure

~75%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...

Structure

~%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...

1,3-Benzodioxole, 5-bromo-6- (bromomethyl)- Structure

1,3-Benzodioxol...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

~%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...

1,3-Benzodioxole, 5-bromo-6- (bromomethyl)- Structure

1,3-Benzodioxol...

Acetanilide Structure

~%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...

Benzanilide Structure

1,3-Benzodioxole, 5-bromo-6- (bromomethyl)- Structure

1,3-Benzodioxol...

~%

[1,3]dioxolo[4,5-j]phenanthridine Structure

[1,3]dioxolo[4,...