4,6-dinitroanthranilic acid and benzo-fused six-membered heterocycles on its basis

Kislyi, K. A.; Samet, A. B.; Семенов, В. В.

doi:10.1134/s1070428002120254

Cited by 6 publications

(5 citation statements)

References 5 publications

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“…Initially, 2,4,6-trinitrobenzoic acid 1 (prepared through oxidation of TNT with dilute HNO 3 8 ) is converted to 2-amino-4,6-dinitrobenzoic acid 2 , with hydrazine in the presence of catalytic amounts of FeCl 3 . Previously the acid 2 was prepared from 1 by the action of TiCl 3 , but the reaction was accompanied by formation of 4-amino-2,6-dinitrobenzoic acid as a side product, and separation of the isomers was troublesome…”

Section: Resultsmentioning

confidence: 99%

“…An additional amount of the product (2.0 g) is collected after acidifying and concentrating the filtrate. Overall yield: 11.2 g (63%), mp 264−265 °C (decomp) (lit . mp 268−270 °C (decomp).…”

Section: Methodsmentioning

confidence: 99%

“…Just in connection with the ongoing research on utilization of polynitroaromatic compounds, − we studied conversion of 2,4,6-trinitrobenzoic acid 7,8 to 2-amino-4,6-dinitrobenzoic acid and further to 5,7-dinitroquinazolones A :

…”

Section: Introductionmentioning

confidence: 99%

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Synthetic Utilization of Polynitroaromatic Compounds. 6. Remarkable Regioselectivity in Nucleophilic Displacement of Aromatic Nitro Groups with Amines

et al. 2008

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5,7-Dinitroquinazoline-4-ones undergo nucleophilic displacement of a nitro group with N-, S-, and O-nucleophiles. In contrast to previously studied dinitro-substituted benzoannulated five- and seven-membered heterocycles (where a high degree of selectivity was observed), these quinazolines mostly yield mixtures of regioisomeric substitution products. At the same time, primary and secondary amines react selectively to afford 5-aminoquinazolones (peri-substitution). A similar effect is observed for some other polynitroaromatic compounds with adjacent nitro and carbonyl groups. This phenomenon is attributed to a stabilization of the intermediate peri-sigma-complex by intramolecular hydrogen bond N(+)-H...O double bond C.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthetic Utilization of Polynitroaromatic Compounds. 6. Remarkable Regioselectivity in Nucleophilic Displacement of Aromatic Nitro Groups with Amines

et al. 2008

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“…5, 6 In particular, it was found that, depending on the conditions, the substitution products of one or both nitro groups can be obtained from 1,3 dinitrodi benz[b, f ] [1,4]oxazepin 11(10H) one (1) (see Refs 2 and 5), and the nitro group in position 3, i.e., the one remote from the point of the ring fusion, was substituted in the first place in all the cases. 5 Benzo fused oxazepines possess various biological ac tivity 7 and are used as the medicines.…”

mentioning

confidence: 99%

“…Earlier, during research on utilization of aromatic polynitro compounds, 1-4 we synthesized mono and dinitro substituted dibenz[b, f ] [1,4]oxazepin 11(10H ) ones and studied their reactions with О and S nucleo philes. 5, 6 In particular, it was found that, depending on the conditions, the substitution products of one or both nitro groups can be obtained from 1,3 dinitrodi benz[b, f ] [1,4]oxazepin 11(10H) one (1) (see Refs 2 and 5), and the nitro group in position 3, i.e., the one remote from the point of the ring fusion, was substituted in the first place in all the cases.…”

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confidence: 99%