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

Synthesis of 5, 6??dimethoxyquinazolin??2 (1H)??ones

JB Press, VT Bandurco, EM Wong…

Index: Press; Bandurco; Wong; et al. Journal of Heterocyclic Chemistry, 1986 , vol. 23, # 6 p. 1821 - 1828

Full Text: HTML

Citation Number: 12

Abstract

Abstract Synthesis of 5, 6-dimethoxyquinazolin-2 (1H)-one derivatives was the subject of investigations leading to the preparation of title compounds 11, 13, 14 and 26. Target quinazolines 1 were synthesized in three ways; the route starting from o-vanillin via the intermediacy of 6-amino-2, 3-dimethoxyacetophenone (19) was used for most of the preparative work. The unexpected formation of an acid-labile dimer of 13 was discovered ...

2,3-Dimethoxy-6-nitrobenzaldehyde ethylene acetal Structure

2,3-Dimethoxy-6...

~94%

2-(1,3-dioxolan-2-yl)-3,4-dimethoxyaniline Structure

2-(1,3-dioxolan...

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Benzaldehyde,3-methoxy-2-[(phenylsulfonyl)oxy] Structure

Benzaldehyde,3-...

~%

2-(1,3-dioxolan-2-yl)-3,4-dimethoxyaniline Structure

2-(1,3-dioxolan...

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(2-formyl-6-methoxy-3-nitrophenyl) benzenesulfonate Structure

(2-formyl-6-met...

~%

2-(1,3-dioxolan-2-yl)-3,4-dimethoxyaniline Structure

2-(1,3-dioxolan...

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3-Methoxysalicylaldehyde Structure

3-Methoxysalicy...

~%

2-(1,3-dioxolan-2-yl)-3,4-dimethoxyaniline Structure

2-(1,3-dioxolan...

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2-Hydroxy-3-methoxy-6-nitrobenzaldehyde, sodium salt Structure

2-Hydroxy-3-met...

~%

2-(1,3-dioxolan-2-yl)-3,4-dimethoxyaniline Structure

2-(1,3-dioxolan...

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Potassium cyanate Structure

Potassium cyanate

1-(6-Amino-2,3-dimethoxyphenyl)ethanone Structure

1-(6-Amino-2,3-...

~94%

Bemarinone Structure

5,5',6,6'-tetramethoxy-4,4'-dimethyl-3',4'-dihydro-2H-[1,4'-biquinazoline]-2,2'(1'H)-dione Structure

5,5',6,6'-tetra...

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2,3-DIMETHOXY-6-NITRO-BENZALDEHYDE Structure

2,3-DIMETHOXY-6...

~%

Bemarinone Structure

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Benzaldehyde,3-methoxy-2-[(phenylsulfonyl)oxy] Structure

Benzaldehyde,3-...

~%

Bemarinone Structure

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(2-formyl-6-methoxy-3-nitrophenyl) benzenesulfonate Structure

(2-formyl-6-met...

~%

Bemarinone Structure

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3-Methoxysalicylaldehyde Structure

3-Methoxysalicy...

~%

Bemarinone Structure

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2-Hydroxy-3-methoxy-6-nitrobenzaldehyde, sodium salt Structure

2-Hydroxy-3-met...

~%

Bemarinone Structure

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3,4-Dihydro-5,6-dimethoxy-4-methyl-2(1H)-quinazolinone Structure

3,4-Dihydro-5,6...

~10%

Bemarinone Structure

(5,6-Dimethoxy-2(1H)-quinazolinon-4-yl)carboxylic acid Structure

(5,6-Dimethoxy-...

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2,3-Dimethoxy-6-nitrobenzaldehyde ethylene acetal Structure

2,3-Dimethoxy-6...

~%

Bemarinone Structure

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6-Amino-2,3-dimethoxy-6-nitrobenzonitrile Structure

6-Amino-2,3-dim...

~%

Bemarinone Structure

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2,3-dimethoxy-6-nitrobenzonitrile Structure

2,3-dimethoxy-6...

~%

Bemarinone Structure

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2(1H)-Quinazolinone, 5,6-dimethoxy Structure

2(1H)-Quinazoli...

~%

Bemarinone Structure

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2-(1,3-dioxolan-2-yl)-3,4-dimethoxyaniline Structure

2-(1,3-dioxolan...

~%

Bemarinone Structure

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N/A Structure

~%

Bemarinone Structure

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6-(N-Carboethoxyamino)-2,3-dimethoxybenzaldehyde ethylene acetal Structure

6-(N-Carboethox...

~%

Bemarinone Structure

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6-Carboethoxyamino-2,3-dimethoxyacetophenone Structure

6-Carboethoxyam...

~%

Bemarinone Structure

5,5',6,6'-tetramethoxy-4,4'-dimethyl-3',4'-dihydro-2H-[1,4'-biquinazoline]-2,2'(1'H)-dione Structure

5,5',6,6'-tetra...

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METHYLMAGNESIUM BROMIDE Structure

METHYLMAGNESIUM...

6-(N-Carbomethoxyamino)-2,3-dimethoxybenzonitrile Structure

6-(N-Carbometho...

~10%

Bemarinone Structure

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2,3-DIMETHOXY-6-NITRO-BENZALDEHYDE Structure

2,3-DIMETHOXY-6...

~%

1-(2,3-Dimethoxy-6-nitrophenyl)ethanone Structure

1-(2,3-Dimethox...

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Benzaldehyde,3-methoxy-2-[(phenylsulfonyl)oxy] Structure

Benzaldehyde,3-...

~%

1-(2,3-Dimethoxy-6-nitrophenyl)ethanone Structure

1-(2,3-Dimethox...

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(2-formyl-6-methoxy-3-nitrophenyl) benzenesulfonate Structure

(2-formyl-6-met...

~%

1-(2,3-Dimethoxy-6-nitrophenyl)ethanone Structure

1-(2,3-Dimethox...

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3-Methoxysalicylaldehyde Structure

3-Methoxysalicy...

~%

1-(2,3-Dimethoxy-6-nitrophenyl)ethanone Structure

1-(2,3-Dimethox...

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2-Hydroxy-3-methoxy-6-nitrobenzaldehyde, sodium salt Structure

2-Hydroxy-3-met...

~%

1-(2,3-Dimethoxy-6-nitrophenyl)ethanone Structure

1-(2,3-Dimethox...

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Benzaldehyde,3-methoxy-2-[(phenylsulfonyl)oxy] Structure

Benzaldehyde,3-...

~%

2,3-dimethoxy-6-nitrobenzonitrile Structure

2,3-dimethoxy-6...

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(2-formyl-6-methoxy-3-nitrophenyl) benzenesulfonate Structure

(2-formyl-6-met...

~%

2,3-dimethoxy-6-nitrobenzonitrile Structure

2,3-dimethoxy-6...

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3-Methoxysalicylaldehyde Structure

3-Methoxysalicy...

~%

2,3-dimethoxy-6-nitrobenzonitrile Structure

2,3-dimethoxy-6...

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2-Hydroxy-3-methoxy-6-nitrobenzaldehyde, sodium salt Structure

2-Hydroxy-3-met...

~%

2,3-dimethoxy-6-nitrobenzonitrile Structure

2,3-dimethoxy-6...

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Benzaldehyde,3-methoxy-2-[(phenylsulfonyl)oxy] Structure

Benzaldehyde,3-...

~58%

(2-formyl-6-methoxy-3-nitrophenyl) benzenesulfonate Structure

(2-formyl-6-met...

2-Hydroxy-3-methoxy-4-nitrobenzaldehyde Benzenesulfonate Structure

2-Hydroxy-3-met...

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3-Methoxysalicylaldehyde Structure

3-Methoxysalicy...

chlorophenylsulfone Structure

chlorophenylsulfone

~90%

Benzaldehyde,3-methoxy-2-[(phenylsulfonyl)oxy] Structure

Benzaldehyde,3-...

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Synthesis and cardiotonic activity of a series of substitute...

[Bandurco, Victor T.; Schwender, Charles F.; Bell, Stanley C.; Combs, Donald W.; Kanojia, Ramesh M.; et al. Journal of Medicinal Chemistry, 1987 , vol. 30, # 8 p. 1421 - 1426]