Synthesis and structure of Meisenheimer adducts in nucleophilic aromatic amination of 4,6-dinitrobenzofuroxan

Stable crystalline σ-complexes (Meisenheimer adducts) were isolated for the first time in the reactions of superelectrophilic 4,6- dinitrobenzofuroxan with dodecyl- and hexadecylamines, and their structure was determined by X-ray analysis. © 2013 Pleiades Publishing, Ltd

Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan

The amination of 4,6-dichloro-5,7-dinitrobenzofuroxan and 4,6-dichloro-5,7-dinitrobenzofurazan with dibenzylamine followed the aromatic nucleophilic substitution pattern (SNAr) and gave products of replacement of both chlorine atoms in the six-membered ring with elimination of hydrogen chloride. Regardless of the reactant ratio, 4,6-dichloro-5,7- dinitrobenzofuroxan was converted into 4,6-bis(dibenzylamino)-5,7- dinitrobenzofuroxan, whereas 4,6-dichloro-5,7-dinitrobenzofurazan under analogous conditions gave rise to unusual bisammonium derivative which lost proton from the amino group on C4 and benzyl group from the amino group on C6; as a result, the corresponding diamine with secondary and tertiary nitrogen atoms was obtained. The structure of the isolated compounds was determined by IR and NMR spectroscopy, elemental analysis, and X-ray analysis; their thermal stability was studied by simultaneous thermogravimetry and differential scanning calorimetry. © 2013 Pleiades Publishing, Ltd

Synthesis and structure of Meisenheimer adducts in nucleophilic aromatic amination of 4,6-dinitrobenzofuroxan

Stable crystalline σ-complexes (Meisenheimer adducts) were isolated for the first time in the reactions of superelectrophilic 4,6- dinitrobenzofuroxan with dodecyl- and hexadecylamines, and their structure was determined by X-ray analysis. © 2013 Pleiades Publishing, Ltd

Synthesis and structure of Meisenheimer adducts in nucleophilic aromatic amination of 4,6-dinitrobenzofuroxan

Stable crystalline σ-complexes (Meisenheimer adducts) were isolated for the first time in the reactions of superelectrophilic 4,6- dinitrobenzofuroxan with dodecyl- and hexadecylamines, and their structure was determined by X-ray analysis. © 2013 Pleiades Publishing, Ltd

Synthesis and structure of Meisenheimer adducts in nucleophilic aromatic amination of 4,6-dinitrobenzofuroxan

Stable crystalline σ-complexes (Meisenheimer adducts) were isolated for the first time in the reactions of superelectrophilic 4,6- dinitrobenzofuroxan with dodecyl- and hexadecylamines, and their structure was determined by X-ray analysis. © 2013 Pleiades Publishing, Ltd

Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan

The amination of 4,6-dichloro-5,7-dinitrobenzofuroxan and 4,6-dichloro-5,7-dinitrobenzofurazan with dibenzylamine followed the aromatic nucleophilic substitution pattern (SNAr) and gave products of replacement of both chlorine atoms in the six-membered ring with elimination of hydrogen chloride. Regardless of the reactant ratio, 4,6-dichloro-5,7- dinitrobenzofuroxan was converted into 4,6-bis(dibenzylamino)-5,7- dinitrobenzofuroxan, whereas 4,6-dichloro-5,7-dinitrobenzofurazan under analogous conditions gave rise to unusual bisammonium derivative which lost proton from the amino group on C4 and benzyl group from the amino group on C6; as a result, the corresponding diamine with secondary and tertiary nitrogen atoms was obtained. The structure of the isolated compounds was determined by IR and NMR spectroscopy, elemental analysis, and X-ray analysis; their thermal stability was studied by simultaneous thermogravimetry and differential scanning calorimetry. © 2013 Pleiades Publishing, Ltd

Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan

The amination of 4,6-dichloro-5,7-dinitrobenzofuroxan and 4,6-dichloro-5,7-dinitrobenzofurazan with dibenzylamine followed the aromatic nucleophilic substitution pattern (SNAr) and gave products of replacement of both chlorine atoms in the six-membered ring with elimination of hydrogen chloride. Regardless of the reactant ratio, 4,6-dichloro-5,7- dinitrobenzofuroxan was converted into 4,6-bis(dibenzylamino)-5,7- dinitrobenzofuroxan, whereas 4,6-dichloro-5,7-dinitrobenzofurazan under analogous conditions gave rise to unusual bisammonium derivative which lost proton from the amino group on C4 and benzyl group from the amino group on C6; as a result, the corresponding diamine with secondary and tertiary nitrogen atoms was obtained. The structure of the isolated compounds was determined by IR and NMR spectroscopy, elemental analysis, and X-ray analysis; their thermal stability was studied by simultaneous thermogravimetry and differential scanning calorimetry. © 2013 Pleiades Publishing, Ltd

Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan

The amination of 4,6-dichloro-5,7-dinitrobenzofuroxan and 4,6-dichloro-5,7-dinitrobenzofurazan with dibenzylamine followed the aromatic nucleophilic substitution pattern (SNAr) and gave products of replacement of both chlorine atoms in the six-membered ring with elimination of hydrogen chloride. Regardless of the reactant ratio, 4,6-dichloro-5,7- dinitrobenzofuroxan was converted into 4,6-bis(dibenzylamino)-5,7- dinitrobenzofuroxan, whereas 4,6-dichloro-5,7-dinitrobenzofurazan under analogous conditions gave rise to unusual bisammonium derivative which lost proton from the amino group on C4 and benzyl group from the amino group on C6; as a result, the corresponding diamine with secondary and tertiary nitrogen atoms was obtained. The structure of the isolated compounds was determined by IR and NMR spectroscopy, elemental analysis, and X-ray analysis; their thermal stability was studied by simultaneous thermogravimetry and differential scanning calorimetry. © 2013 Pleiades Publishing, Ltd