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

Studies in SRN1 series. Part 14. Direct synthesis of benzo [c] phenanthridines and benzo [c] phenanthridones via SRN1 reactions

…, H Ginsburg, L Quintero-Cortes, G Roussi

Index: Beugelmans, Rene; Chastanet, Jacqueline; Ginsburg, Helene; Quintero-Cortes, Leticia; Roussi, Georges Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4933 - 4938

Full Text: HTML

Citation Number: 62

Abstract

A straightforward and high-yield route to the 11, 12-dihydrobenzo [c] phenanthridine (3) and 11, 12-dihydrobenzo [c] phenanthridone (14) ring systems is based upon an SRN~ reaction between 2-halobenzylamines 1 or 2-halobenzoic acids 11 and enolates derived from tetralones 2. The efficient dehydrogenation of 3 or 14 gives the benzo [clphenanthridines 4 or benzo [c] phenanthridones 15. Use of properly substituted reactants leads to nitidine, ...

N/A Structure

~65%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

N-[(3,4-dimetho...

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

veratraldehyde Structure

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

1-(3,4-Dimethoxyphenyl)methanamine Structure

1-(3,4-Dimethox...

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

N-acetyl-4,5-dimethoxy-2-iodobenzylamine Structure

N-acetyl-4,5-di...

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

4-(3,4-Dimethoxyphenyl)butanoic acid Structure

4-(3,4-Dimethox...

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

6,7-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one Structure

6,7-Dimethoxy-3...

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

N/A Structure

~%

Benzo[c]phenanthridine,2,3,8,9-tetramethoxy- Structure

Benzo[c]phenant...

4-Isopropoxy-3-methoxybenzaldehyde Structure

4-Isopropoxy-3-...

~96%

(NE)-N-[(3-methoxy-4-propan-2-yloxyphenyl)methylidene]hydroxylamine Structure

(NE)-N-[(3-meth...

Vanillin Structure

~%

(NE)-N-[(3-methoxy-4-propan-2-yloxyphenyl)methylidene]hydroxylamine Structure

(NE)-N-[(3-meth...

piperonal Structure

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

4-(1,3-benzodioxol-5-yl)but-3-enoic acid Structure

4-(1,3-benzodio...

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

4-(1,3-benzodioxol-5-yl)butanoic acid Structure

4-(1,3-benzodio...

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

N-[(3,4-dimetho...

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

1-(3,4-Dimethoxyphenyl)methanamine Structure

1-(3,4-Dimethox...

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

N/A Structure

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

N-acetyl-4,5-dimethoxy-2-iodobenzylamine Structure

N-acetyl-4,5-di...

~%

2,3-dimethoxy-[1,3]benzodioxolo[5,6-c]phenanthridine Structure

2,3-dimethoxy-[...

1,3-Benzodioxol-5-Ylmethylamine Structure

1,3-Benzodioxol...

Ethanoic anhydride Structure

Ethanoic anhydride

~99%

N-(benzo[1,3]dioxol-5-ylmethyl)acetamide Structure

N-(benzo[1,3]di...

Isovanillin Structure

~%

1(2H)-Naphthalenone,3,4-dihydro-6-hydroxy-7-methoxy- Structure

1(2H)-Naphthale...

veratraldehyde Structure

~%

1(2H)-Naphthalenone,3,4-dihydro-6-hydroxy-7-methoxy- Structure

1(2H)-Naphthale...

N/A Structure

~%

1(2H)-Naphthalenone,3,4-dihydro-6-hydroxy-7-methoxy- Structure

1(2H)-Naphthale...

4-(3,4-Dimethoxyphenyl)butanoic acid Structure

4-(3,4-Dimethox...

~%

1(2H)-Naphthalenone,3,4-dihydro-6-hydroxy-7-methoxy- Structure

1(2H)-Naphthale...

(NE)-N-[(3-methoxy-4-propan-2-yloxyphenyl)methylidene]hydroxylamine Structure

(NE)-N-[(3-meth...

~95%

(3-methoxy-4-propan-2-yloxyphenyl)methanamine,hydrochloride Structure

(3-methoxy-4-pr...

4-Isopropoxy-3-methoxybenzaldehyde Structure

4-Isopropoxy-3-...

~%

(3-methoxy-4-propan-2-yloxyphenyl)methanamine,hydrochloride Structure

(3-methoxy-4-pr...

Vanillin Structure

~%

(3-methoxy-4-propan-2-yloxyphenyl)methanamine,hydrochloride Structure

(3-methoxy-4-pr...

N/A Structure

~89%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

Isovanillin Structure

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

4-(3,4-Dimethoxyphenyl)butanoic acid Structure

4-(3,4-Dimethox...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

4-(3-hydroxy-4-methoxyphenyl)butanoic acid Structure

4-(3-hydroxy-4-...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

N-[(3,4-dimetho...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

1(2H)-Naphthalenone,3,4-dihydro-6-hydroxy-7-methoxy- Structure

1(2H)-Naphthale...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

veratraldehyde Structure

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

6,7-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one Structure

6,7-Dimethoxy-3...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

N/A Structure

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

1-(3,4-Dimethoxyphenyl)methanamine Structure

1-(3,4-Dimethox...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

6-isopropoxy-7-methoxy-1-tetralone Structure

6-isopropoxy-7-...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

(2-Iodo-4,5-dimethoxyphenyl)methanamine Structure

(2-Iodo-4,5-dim...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

N/A Structure

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

N-acetyl-4,5-dimethoxy-2-iodobenzylamine Structure

N-acetyl-4,5-di...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

2-isopropoxy-3,8,9-trimethoxy-11,12-dihydrobenzo[c]phenanthridine Structure

2-isopropoxy-3,...

~%

3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one Structure

3,8,9-trimethox...

piperonal Structure

~%

7,8-Dihydronaphtho[2,3-d][1,3]dioxol-5(6H)-one Structure

7,8-Dihydronaph...

N/A Structure

~%

7,8-Dihydronaphtho[2,3-d][1,3]dioxol-5(6H)-one Structure

7,8-Dihydronaph...

2,3-dimethoxy-12,13-dihydrobenzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-1...

~75%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

1,3-Benzodioxol-5-Ylmethylamine Structure

1,3-Benzodioxol...

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

N-(benzo[1,3]dioxol-5-ylmethyl)acetamide Structure

N-(benzo[1,3]di...

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

veratraldehyde Structure

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

2-iodo-4,5-(methylenedioxy)-N-acetylbenzylamine Structure

2-iodo-4,5-(met...

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

4-(3,4-Dimethoxyphenyl)butanoic acid Structure

4-(3,4-Dimethox...

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

N/A Structure

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

2-iodo-4,5-(methylenedioxy)benzylamine Structure

2-iodo-4,5-(met...

~%

2,3-dimethoxy-benzo[c][1,3]dioxolo[4,5-j]phenanthridine Structure

2,3-dimethoxy-b...

Ethanoic anhydride Structure

Ethanoic anhydride

1-(3,4-Dimethoxyphenyl)methanamine Structure

1-(3,4-Dimethox...

~%

N-[(3,4-dimethoxyphenyl)methyl]acetamide Structure

N-[(3,4-dimetho...

piperonal Structure

~%

4-(1,3-benzodioxol-5-yl)butanoic acid Structure

4-(1,3-benzodio...

veratraldehyde Structure

~%

1(2H)-Naphthalenone,3,4-dihydro-7-hydroxy-6-methoxy- Structure

1(2H)-Naphthale...

N/A Structure

~%

1(2H)-Naphthalenone,3,4-dihydro-7-hydroxy-6-methoxy- Structure

1(2H)-Naphthale...

4-(3,4-Dimethoxyphenyl)butanoic acid Structure

4-(3,4-Dimethox...

~%

1(2H)-Naphthalenone,3,4-dihydro-7-hydroxy-6-methoxy- Structure

1(2H)-Naphthale...

(Z)-Ethyl 2-phenyl-1-(2-vinylphenyl) vinylcarbamates. Part 1...

[Treus, Monica; Salas, Cristian O.; Gonazalez, Marcos A.; Estevez, Juan C.; Tapia, Ricardo A.; Estevez, Ramon J. Tetrahedron, 2010 , vol. 66, # 52 p. 9986 - 9995]