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

1, 3, 4??Benzotriazepinones. Formation and rearrangement

P Scheiner, L Frank, I Giusti, S Arwin…

Index: Scheiner; Frank; Giusti; et al. Journal of Heterocyclic Chemistry, 1984 , vol. 21, # 6 p. 1817 - 1824

Full Text: HTML

Citation Number: 33

Abstract

Abstract Anthranilic hydrazide reacts with orthoesters to produce mixtures of 3 products: 3, 4- dihyro-5H-1, 3, 4-benzotriazepin-5-ones (1), 3-amino-3, 4-dihydro-4-quinazolinones (2) and 2-(2-aminophenyl)-1, 3, 4-oxadiazoles (4). The origin of these materials has been investigated. Product distributions depend on the nature of substituents, solvent and time. In ethanol benzotriazepinones are kinetically favored, but formed reversibly they ...

Trimethyl orthobenzoate Structure

Trimethyl ortho...

~%

3-Amino-2-phenyl-4(3H)-quinazolinone Structure

3-Amino-2-pheny...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

Trimethyl orthobenzoate Structure

Trimethyl ortho...

~%

3-Amino-2-phenyl-4(3H)-quinazolinone Structure

3-Amino-2-pheny...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

Trimethyl orthobenzoate Structure

Trimethyl ortho...

~8%

3-Amino-2-phenyl-4(3H)-quinazolinone Structure

3-Amino-2-pheny...

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-phenyl- Structure

5H-1,3,4-Benzot...

Detail

Triethyl orthoacetate Structure

Triethyl orthoa...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~47%

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-methyl- Structure

5H-1,3,4-Benzot...

1-(2-Aminobenzoyl)-2-(1-dimethylaminoethylidene)hydrazine Structure

1-(2-Aminobenzo...

~21%

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-methyl- Structure

5H-1,3,4-Benzot...

Benzenamine, 2-(5-methyl-1,3,4-oxadiazol-2-yl)- Structure

Benzenamine, 2-...

Triethyl orthoacetate Structure

Triethyl orthoa...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~52%

2-methyl-3-amino-4-quinazolone Structure

2-methyl-3-amin...

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-methyl- Structure

5H-1,3,4-Benzot...

Detail

Ethyl 4-amino-1H-imidazole-5-carboxylate Structure

Ethyl 4-amino-1...

~93%

1H-Imidazole-4-carboxylicacid,5-amino-,hydrazide(9CI) Structure

1H-Imidazole-4-...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

Trimethyl orthobenzoate Structure

Trimethyl ortho...

~67%

Benzenamine,2-(5-phenyl-1,3,4-oxadiazol-2-yl)- Structure

Benzenamine,2-(...

Triethyl orthoformate Structure

Triethyl orthof...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~8%

2-(1,3,4-oxadiazol-2-yl)aniline(SALTDATA: FREE) Structure

2-(1,3,4-oxadia...

Triethyl orthoformate Structure

Triethyl orthof...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~9%

3-Amino-4(3H)-quinazolinone Structure

3-Amino-4(3H)-q...

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

Detail

1-(2-Aminobenzoyl)-2-dimethylaminomethylene Hydrazine Structure

1-(2-Aminobenzo...

~43%

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

2-(1,3,4-oxadiazol-2-yl)aniline(SALTDATA: FREE) Structure

2-(1,3,4-oxadia...

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

~%

3-Amino-4(3H)-quinazolinone Structure

3-Amino-4(3H)-q...

2-(1,3,4-oxadiazol-2-yl)aniline(SALTDATA: FREE) Structure

2-(1,3,4-oxadia...

Triethyl orthoformate Structure

Triethyl orthof...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~42%

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

Triethyl orthoformate Structure

Triethyl orthof...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~36%

3-Amino-4(3H)-quinazolinone Structure

3-Amino-4(3H)-q...

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

Detail

1-(2-Aminobenzoyl)-2-dimethylaminomethylene Hydrazine Structure

1-(2-Aminobenzo...

~54%

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

2-(1,3,4-oxadiazol-2-yl)aniline(SALTDATA: FREE) Structure

2-(1,3,4-oxadia...

Triethyl orthoacetate Structure

Triethyl orthoa...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~%

2-methyl-3-amino-4-quinazolone Structure

2-methyl-3-amin...

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-methyl- Structure

5H-1,3,4-Benzot...

~99%

2-methyl-3-amino-4-quinazolone Structure

2-methyl-3-amin...

2-(1-Ethoxyethylideneamino)benzamide Structure

2-(1-Ethoxyethy...

~99%

2-Methylquinazolin-4-ol Structure

2-Methylquinazo...

Triethyl orthoformate Structure

Triethyl orthof...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

~84%

3-Amino-4(3H)-quinazolinone Structure

3-Amino-4(3H)-q...

3,4-dihydro-1,3,4-benzotriazepin-5-one Structure

3,4-dihydro-1,3...

~99%

3-Amino-4(3H)-quinazolinone Structure

3-Amino-4(3H)-q...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

Trimethyl orthobenzoate Structure

Trimethyl ortho...

~46%

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-phenyl- Structure

5H-1,3,4-Benzot...

2-aminobenzhydrazide Structure

2-aminobenzhydrazide

Trimethyl orthobenzoate Structure

Trimethyl ortho...

~55%

3-Amino-2-phenyl-4(3H)-quinazolinone Structure

3-Amino-2-pheny...

5H-1,3,4-Benzotriazepin-5-one,3,4-dihydro-2-phenyl- Structure

5H-1,3,4-Benzot...

Detail

Design and synthesis of some new quinazolin-4-(3H)-ones as a...

[Amir, Mohd; Ali, Israr; Hassan, Mohd Zaheen Archives of Pharmacal Research, 2013 , vol. 36, # 1 p. 61 - 68]

Design, synthesis and potential 6 Hz psychomotor seizure tes...

[Kumar, Praveen; Shrivastava, Birendra; Pandeya, Surendra N.; Stables, James P. European Journal of Medicinal Chemistry, 2011 , vol. 46, # 4 p. 1006 - 1018]

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[Kumar, Praveen; Shrivastava, Birendra; Pandeya, Surendra N.; Stables, James P. European Journal of Medicinal Chemistry, 2011 , vol. 46, # 4 p. 1006 - 1018]