Studies on the Reactions of Heterocyclic Compounds. IV. Preparations and Reactions of Heterocyclic N-Ylides

• Published in: Chemical & pharmaceutical bulletin Vol. 18; no. 12; pp. 2489 - 2498
• Main Authors: KOBAYASHI, YOSHIRO, KUTSUMA, TERUO, MORINAGA, KUNIO, FUJITA, MAMORU, HANZAWA, YUJI
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1970; Japan Science and Technology Agency
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.18.2489

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).