Springer Nature
Chemistry of Heterocyclic Compounds
,  том 8 ,  издание 5 ,  страницы 632-635

Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones

Тип публикации: Journal Article
Дата публикации: 1972-05-01
Springer Nature
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SJR: 0.243
CiteScore: 2.7
Impact factor: 1
ISSN: 00093122, 15738353
Organic Chemistry
Краткое описание
The reaction of 4-nitro-o-phenylenediamine (I) with acetoacetic ester at room temperature under acid catalysis gives ethyl 3-(2-amino-5-nitrophenylamino)crotonate (II), which is readily cyclized to 7-nitro-4-methyl-2,3-dihydro-1H-1,5-benzo-2-diazepinone (III) on heating with alkaline agents. The reaction of I with acetoacetic ester in refluxing xylene gives isomeric 8-nitro-4-methyl-2,5-dihydro-1H-1,5-benzo-2-diazepinone (IVa) or 8-nitro-4-methyl-2,3-dihydro-1H-1,5-benzo-2-diazepinone (IVb), which are readily interconverted. The synthesis of IV is complicated by the side formation of 5-nitro-2-methylbenzimidazole (V) and thermal rearrangement of IVa and IVb to 5-nitro-1-isopropenylbenzimidazolone (VI). 6-Nitro-1-isopropenylbenzimidazolone (VII) is similarly obtained on heating III.
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Kost A. N. et al. Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones // Chemistry of Heterocyclic Compounds. 1972. Vol. 8. No. 5. pp. 632-635.
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Kost A. N., Solomko Z. F., Budylin V. A., Semenova T. S. Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones // Chemistry of Heterocyclic Compounds. 1972. Vol. 8. No. 5. pp. 632-635.
RIS |
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TY - JOUR
DO - 10.1007/bf00488164
UR - https://doi.org/10.1007/bf00488164
TI - Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones
T2 - Chemistry of Heterocyclic Compounds
AU - Kost, A. N.
AU - Solomko, Z F
AU - Budylin, V A
AU - Semenova, T S
PY - 1972
DA - 1972/05/01
PB - Springer Nature
SP - 632-635
IS - 5
VL - 8
SN - 0009-3122
SN - 1573-8353
ER -
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@article{1972_Kost,
author = {A. N. Kost and Z F Solomko and V A Budylin and T S Semenova},
title = {Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones},
journal = {Chemistry of Heterocyclic Compounds},
year = {1972},
volume = {8},
publisher = {Springer Nature},
month = {may},
url = {https://doi.org/10.1007/bf00488164},
number = {5},
pages = {632--635},
doi = {10.1007/bf00488164}
}
MLA
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Kost, A. N., et al. “Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones.” Chemistry of Heterocyclic Compounds, vol. 8, no. 5, May. 1972, pp. 632-635. https://doi.org/10.1007/bf00488164.