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

Synthesis and chemistry of 1, 3-diazabiphenylenes

V Bakthavachalam, M d'Alarcao…

Index: Bakthavachalam, Venkatesalu; d'Alarcao, Marc; Leonard, Nelson J. Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 289 - 295

Full Text: HTML

Citation Number: 15

Abstract

Two independent syntheses of the 1, 3-diazabiphenylene ring system have been developed. The first of these involves thermal extrusion of nitrogen from a condensed pyridazine precursor, and the second utilizes a diethynylpyrimidine in a cobalt-catalyzed co- oligomerizatioh reaction. The 1, 3-diazabiphenylenes undergo facile transformations to isoquinolines upon treatment with either acid or base. The intermediacy of 1, 3- ...

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

~72%

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~%

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

4-Methoxy-1,3-diazabiphenylene Structure

4-Methoxy-1,3-d...

~%

1,3-dimethoxyisoquinoline Structure

1,3-dimethoxyis...

(1,3-dimethoxy-6-trimethylsilylisoquinolin-7-yl)-trimethylsilane Structure

(1,3-dimethoxy-...

~%

1,3-dimethoxyisoquinoline Structure

1,3-dimethoxyis...

6,7-Bis(trimethylsilyl)-4-methoxy-1,3-diazabiphenylene Structure

6,7-Bis(trimeth...

~%

1,3-dimethoxyisoquinoline Structure

1,3-dimethoxyis...

Methanol Structure

4-Methoxy-1,3-diazabiphenylene Structure

4-Methoxy-1,3-d...

~%

1,3-dimethoxyisoquinoline Structure

1,3-dimethoxyis...

(1,3-dimethoxy-6-trimethylsilylisoquinolin-7-yl)-trimethylsilane Structure

(1,3-dimethoxy-...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~%

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

~%

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

Ethyl formate Structure

~%

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

~87%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

~%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

~%

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

~13%

2-(2-chloroethynyl)benzonitrile Structure

2-(2-chloroethy...

4-Chloro-1,3-diazabiphenylene Structure

4-Chloro-1,3-di...

2-(2-cyanoethynyl)benzonitrile Structure

2-(2-cyanoethyn...

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

~8%

2-(2-chloroethynyl)benzonitrile Structure

2-(2-chloroethy...

4-Chloro-1,3-diazabiphenylene Structure

4-Chloro-1,3-di...

2-(2-cyanoethynyl)benzonitrile Structure

2-(2-cyanoethyn...

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

N,N-Bis(trimethylsilyl)acetamide Structure

N,N-Bis(trimeth...

~77%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

~%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

~%

trimethyl(pyrimido[4,5-c]cinnolin-1-yloxy)silane Structure

trimethyl(pyrim...

2-[4-methoxy-6-(2-trimethylsilylethynyl)pyrimidin-5-yl]ethynyl-trimethylsilane Structure

2-[4-methoxy-6-...

~%

4,5-diethynyl-6-methoxypyrimidine Structure

4,5-diethynyl-6...

5-(2-bromoethynyl)-4-iodo-6-methoxypyrimidine Structure

5-(2-bromoethyn...

~%

4,5-diethynyl-6-methoxypyrimidine Structure

4,5-diethynyl-6...

Methanol Structure

6,7-Bis(trimethylsilyl)-4-methoxy-1,3-diazabiphenylene Structure

6,7-Bis(trimeth...

~73%

(1,3-dimethoxy-6-trimethylsilylisoquinolin-7-yl)-trimethylsilane Structure

(1,3-dimethoxy-...

Methanol Structure

4-Methoxy-1,3-diazabiphenylene Structure

4-Methoxy-1,3-d...

~%

1,3-dimethoxyisoquinoline Structure

1,3-dimethoxyis...

(1,3-dimethoxy-6-trimethylsilylisoquinolin-7-yl)-trimethylsilane Structure

(1,3-dimethoxy-...

Sodium Methylate Structure

Sodium Methylate

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

~84%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

~%

1-methoxypyrimido[4,5-c]cinnoline Structure

1-methoxypyrimi...

Sodium Methylate Structure

Sodium Methylate

4,6-dichloro-5-(2,2-dibromoethenyl)pyrimidine Structure

4,6-dichloro-5-...

~74%

5-(2-bromoethynyl)-4-chloro-6-methoxypyrimidine Structure

5-(2-bromoethyn...

4,6-Dichloro-5-pyrimidinecarbaldehyde Structure

4,6-Dichloro-5-...

~%

5-(2-bromoethynyl)-4-chloro-6-methoxypyrimidine Structure

5-(2-bromoethyn...

4,6-dichloro-5-(2,2-dibromoethenyl)pyrimidine Structure

4,6-dichloro-5-...

~%

2-(4-chloro-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-chloro-6-m...

4,6-Dichloro-5-pyrimidinecarbaldehyde Structure

4,6-Dichloro-5-...

~%

2-(4-chloro-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-chloro-6-m...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

5-(2-bromoethynyl)-4-chloro-6-methoxypyrimidine Structure

5-(2-bromoethyn...

~%

2-(4-chloro-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-chloro-6-m...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

5-(2-bromoethynyl)-4-iodo-6-methoxypyrimidine Structure

5-(2-bromoethyn...

~%

2-(4-bromo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-bromo-6-me...

2-(4-iodo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-iodo-6-met...

5-(2,2-dibromoethenyl)-4,6-diiodopyrimidine Structure

5-(2,2-dibromoe...

~%

2-(4-bromo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-bromo-6-me...

4,6-Dichloro-5-pyrimidinecarbaldehyde Structure

4,6-Dichloro-5-...

~%

2-(4-bromo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-bromo-6-me...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

5-(2-bromoethynyl)-4-iodo-6-methoxypyrimidine Structure

5-(2-bromoethyn...

~%

2-(4-bromo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-bromo-6-me...

2-(4-iodo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-iodo-6-met...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~78%

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~80%

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~96%

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

4,6-dichloro-5-(2,2-dibromoethenyl)pyrimidine Structure

4,6-dichloro-5-...

~%

2-(4-bromo-6-methoxypyrimidin-5-yl)ethynyl-trimethylsilane Structure

2-(4-bromo-6-me...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

5-(2-bromoethynyl)-4-iodo-6-methoxypyrimidine Structure

5-(2-bromoethyn...

TMS-acetylene Structure

~%

2-[4-methoxy-6-(2-trimethylsilylethynyl)pyrimidin-5-yl]ethynyl-trimethylsilane Structure

2-[4-methoxy-6-...

Sodium Methylate Structure

Sodium Methylate

4-Chloro-1,3-diazabiphenylene Structure

4-Chloro-1,3-di...

~83%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

4-Methyl-3-nitrocinnoline Structure

4-Methyl-3-nitr...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

nitroformaldehyde o-acetylphenylhydrazone Structure

nitroformaldehy...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

3-aminocinnoline-4-carboxamide Structure

3-aminocinnolin...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

4H-pyrimido[4,5-c]cinnolin-1-one Structure

4H-pyrimido[4,5...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

3-nitrocinnoline-4-carbonitrile Structure

3-nitrocinnolin...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

3-nitro-4-(nitrosomethylidene)-1H-cinnoline Structure

3-nitro-4-(nitr...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

3-nitrocinnoline-4-carboxamide Structure

3-nitrocinnolin...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

Sodium Methylate Structure

Sodium Methylate

1-Chloro-4-isoquinolinecarbonitrile Structure

1-Chloro-4-isoq...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...

1-chloropyrimido[4,5-c]cinnoline Structure

1-chloropyrimid...

~%

1-methoxyisoquinoline-4-carbonitrile Structure

1-methoxyisoqui...