Activated anilide in heterocyclic synthesis: Synthesis of new hydrazo, dihydropyridazine, tetrahydropyridine, dihydropyridine and pyranopyridine derivatives

Abstract

A series of new hydrazo, dihydropyridazine, tetrahydropyridine, dihydropyridine and pyranopyridine derivatives with known biological activity have been prepared through the reactions of 3-oxo-3-phenyl-N-(pyridine-3-yl) propanamide 3 and enaminonitrile 17 with some electrophilic reagents, nucleophilic reagents, and aryl diazonium salts. The newly synthesized compounds were characterized by IR, 1 H NMR and mass spectral studies.

The applications of β‐keto amides for heterocycle synthesis

“…3‐Oxo‐3‐phenyl‐ N ‐(pyridine‐3‐yl) propanamides 433 could react with arenediazonium salts to afford hydrazones 435 in excellent yields. Hafiz et al used these hydrazones to undergo rapid condensation with malononitrile and NH 4 OAc to form corresponding dihydropyridazine‐3‐carboxamides 437 via intermediate 436 (Scheme 108) [191].…”

Green Synthesis of Pyrano[3,2-c]pyridine Derivatives in Ionic Liquids

“…另外还被用 作缺氧诱导因子(HIF)抑制剂 [5] 及钾通道拮抗剂 [6] . 尽管 已有很多文献报道过其合成方法, 主要包括磺酸催化下 丙二腈和 3,5-二芳亚甲基-N-甲基吡啶-4-酮的反应 [7] , Zr(IV)络合物催化间苯二酚、丙二腈、芳醛和环己酮的 反应 [8] , 3-氧代-3-苯基-N-(3-吡啶基)丙酰胺和烯胺腈的 反应 [9] , 以氨基酸和不饱和醇为原料的[4＋2]环加成反 应 [10] , 及三乙胺催化下醛、吡啶酮和丙二腈的溶剂反应 [11] 等多种方法 [12] . 但这些方法具有或属于多步反应、或 原料不易得、或需要昂贵的催化剂参与、或使用有机溶 剂作为反应介质等不足.…”