Synthesis of (Z)-2-(4-(Arylimino)-3,4-Dihydroquinazolin-2(1H)-Ylidene)-1H-Indene-1,3(2H)Dione Using 2-Amino-N′-Aryl-Benzimidamides as a Starting Material

Abstract

The reaction between 2-amino-N'-arylbenzimidamide derivatives (3a-g) and 2-dicyanomethyleneindan-1,3-dione (4, CNIND) is described. The product that was obtained in moderate to good yields via CT-complexation is identified as (Z)-2-[4-(arylimino)-3,4-dihydroquinazolin-2(1H)-ylidene]-1H-indene-1,3(2H)-dione (5a-g).

Condensation Reactions of 2-Aminobenzohydrazide with Various Carbonyl Compounds

“…Furthermore, a multiplet was present in the region of δ = 1.80 -3.35 ppm due to the methylene protons of the electrophile, in addition to a singlet signal at δ = 4.75 ppm for the benzyl -CH 2 protons and a multiplet at δ = 6.70 -7.65 ppm for the aromatic protons. Moreover, the spiro-carbon atom of 8 resonated in the 13 C NMR spectrum at δ = 114.00 ppm, and the carbonyl carbon atom resonated at 163.00 ppm. The molecular formula of compound 8 is supported by elemental analysis and a mass spectrum that gave the expected molecular ion peak and fragmentation patterns.…”

“…The 1 H NMR spectrum of 14 confirmed the disappearance of the NH 2 group, while the NH proton resonated at 7.59 ppm. The spiro-carbon atom resonated in the 13 C NMR spectrum at δ = 100.00 ppm. Furthermore, the signals of the carbonyl carbon atoms and the C=N carbon atom appeared at 198.22, 167.55 and 169.55 ppm, respectively.…”

“…IR spectra were measured using a Bruker Tensor 27 instrument. 1 H NMR (300 or 400 MHz) and 13 C NMR (75 or 101 MHz) spectra were recorded in [D 6 ]DMSO on Bruker Avance II-300 and Avance DRX-400 spectrometers with TMS (for 1 H) or the solvent (for 13 C, δ C = 77.01 ppm) as the internal standards. Mass spectral measurements (EI, 70 eV) were performed using a Finnigan MAT 8430 spectrometer.…”

The reaction of 2-amino- N ′-arylbenzamidines with tetracyanoethene reinvestigated: routes to imidazoles, quinazolines and quinolino[2′,3′:4,5]imidazo[1,2- c ]quinazoline-8-carbonitrile

“…31 The structures were solved by direct methods using SIR92 32 and refined on F 2 using fullmatrix least squares using SHELXL97. 33 4-Imino-3-(4-methoxyphenyl)-3,4-dihydroquinazoline-2-carbonitrile (9c), CDCl 3 , 13 C-NMR 110 112 114 116 118 120 122 124 126 128 130 132 134 136 138 140 142 144 146 148 150 152 154 156 158 160 162 f1 ( 3-(4-Chlorophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitrile (9e), CDCl 3 , 13 C-NMR 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 f1 ( 2-[2-(2-Aminophenyl)-5-imino-1-phenyl-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile (11a), DMSO-d 6 , 13 2-(2-(2-Aminophenyl)-5-imino-1-(p-tolyl)-1,5-dihydro-4H-imidazol-4-ylidene)malononitrile (11b), DMSO-d 6 , 13 2-[2-(2-Aminophenyl)-5-imino-1-(4-methoxyphenyl)-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile (11c), DMSO-d 6 , 13 2-[2-(2-Aminophenyl)-1-(4-fluorophenyl)-5-imino-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile (11d), DMSO-d 6 , 13 2-[2-(2-Aminophenyl)-1-(4-chlorophenyl)-5-imino-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile (11e), DMSO-d 6 , 13 2-[2-Aminophenyl)-1-(4-bromophenyl)-5-imino-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile 2-[2-(2-Aminophenyl)-1-(4-bromophenyl)-5-imino-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile (1f), DMSO-d 6 , 13 2-[2-(2-Aminophenyl)-1-(3,4-dimethoxyphenyl)-5-imino-1,5-dihydro-4H-imidazol-4-ylidene]malononitrile (11g), DMSO-d 6 , 13 …”

“…2-Nitro-N'-pheny-N-(1,2,2-tricyanovinyl)benzamidine (26), CDCl 3 2-Nitro-N'-pheny-N-(1,2,2-tricyanovinyl)benzamidine (26), CDCl 3 , 13 …”