Chemistry of sulfonylmethyl isocyanides. 12. Base-induced cycloaddition of sulfonylmethyl isocyanides to carbon,nitrogen double bonds. Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl chlorides

Synthesis and Bleaching Activity of 1,5-Disubstituted Imidazoles

“…(4). To a suspension of 0.3 g of sodium hydride (60% in oil) in 20 ml of dimethylfomamide (DMF) was added dropwise I g of compound 2 in 15 ml of DMF.…”

“…The 1,5-disubstituted imidazoles were prepared according to procedures described by van Leusen et al 4 ) and the modified method reported previously. 5) Most of the compounds were prepared by the method outlined in Fig.…”

“…A mixture of 0.9 g of 5-(4-hydroxyphenyl)-I-propargylimidazole, 0.3g of NaOH, O.lg of benzyltri-n-butylammonium bromide and 0.7 g of benzyl chloride in 10 ml of dichloromethane and 10 ml of water was stirred for 2 days at room temperature. The dichloromethane solution was washed with brine, dried over Na z S0 4 Bioassay. An acetone solution (I ml) containing the proper amount of a test compound was poured on to a filter paper in a Petri dish of 9 em in diameter.…”

Synthesis and Insect Growth Regulatory Activity of 1,5-Disubstituted Imidazoles with Non-terpene Chains

“…NMR D: 1.42 (6H, d, J= 7 Hz), 4.40 (JH, m), 6.96--7.69 (II H,m),Anal,Found: C,77.83;H,6,51;N,10.11 %,Calcd,for C18H18N20: C,77.67;H,6,52; N, 10,06%, (7), A mixture of 4.9 g of 3-hydroxybenzaldehyde, 2.4 g of isopropylamine and 12g of anhydrous MgS04 in 40ml of dichloromethane was refiuxed for 3 hr. The MgS04 was filtered ofT, and the filtrate was concentrated under reduced pressure, The residue was dissolved in 40 ml of methanol, and to the mixture was added 16 g of anhydrous K 2 C03 and 10 g of TosMIc' After refiuxing for 3 hr, the solvent was evaporated, and 150 ml of water was added to the residue, The precipitate was collected by filtration and recrystallized from ethyl acetate to afford 4.76 g (58,5%) of7, mp 170-172°C, NMR 6: 1.45 (6H,d,J=7Hz),4,50 (lH,m),6,m),7,80 (lH,s),Anal,Found: C,71.16;H,6,81;N,13,83%,Calcd,for C12H14N20: C,71.26;H,6,98;N,13,85%,, To a suspension of 0,2 g of sodium hydride (60% in oil) in 10mi of dimethylformamide at 0-5°C was added 2.2 g of compound 7. and the mixture was stirred for I hr at room temperature. To the ice-cooled mixture was added 1.5 g of benzyl chloride, After stirring for 10 hr at room temperature, 50 ml of water was added to the mixture, and the product was extracted with ether.…”

“…The ether solution was washed with brine and dried over Na2S04 . After removal of the solvent, the residue was chromatographed on silica gel by eluting with hexane-cthyl acetate (2: I) and ethyl acetate, Concentration of the ethyl acetate eluate under reduced pressure gave 1.28 g (40.3%) of 8 as an oil which crystallized after keeping in a refrigerator and was recrystallized from ethyl acetate, mp 113-114°C, NMR b: 1.40 (6H,d,J = 8 Hz),4,36 (lH,m),5.11 (2H,s),6,m),7,68 (lH,s),Anal. Found: C,77.99;H,6,91;N,9,57%,Calcd,for C19H20N20: C,78,05;H,6,90;N,9,58%, Compounds 9 and 10 were similarly prepared from salicylaldehyde and 4-hydroxybenzaldehyde, respectively,…”