Abstract
The reaction of di-substituted methyl bromides such as dimethyl bromomalonate (IIa), bromomalonamide (IIb), bromocyanoacetamide (IIc), and methyl bromocyanoacetate (IId) with aromatic amines (pyridine, isoquinoline, and 1, 6-naphthyridine) gave stable N-ylides, IVa-IVd, VIa, VIb, and VIIa. From the reaction of bromomalononitrile (IIe) and quinoline or isoquinoline afforded diquinolinium-(VIII) and diisoquinolinium pentacyanopropenide (IX). From the reaction of IId with quinolines in MeOH, azirino [1, 2-a]-cyclopropa [c] quinoline derivatives (Xa and Xc) with new ring system were given. When treated with hydrogen chloride in MeOH, Xa was converted to dimethyl 3-quinolinemalonate (XII). When IVd was treated with sodium methoxide in DMF, methyl α-cyano-[1, (4H), 4'-bipyridine]-△α, 4-acetate (XVI) was produced. VIc, VIb, and VIIb, when treated with sodium methoxide in MeOH, gave fused imidazole derivatives (XVIII, XIX, and XX).
