Molecular iodine-catalyzed and air-mediated tandem synthesis of quinolines via three-component reaction of amines, aldehydes, and alkynes

Recent Advances in Metal-Free Quinoline Synthesis

“…Lin et al [24] reported a molecular iodine-catalyzed version of the Povarov reaction (Figure 11), in which quinoline derivatives were obtained directly from aniline (1), aldehyde (9), and alkyne (18) precursors. The aniline 1 first forms a Schiff base with the aldehyde 9, which then coordinates with the Lewis acidic I 2 .…”

A Green, Solvent-Free One-Pot Synthesis of Disubstituted Quinolines via A3-Coupling Using 1 Mol% FeCl3

“…A melting range was observed between 134-136°C, which correlated to the literature melting range of 135-136°C. [89] The disubstituted quinolines were synthesized in good to excellent yields with the results summarized in the table below. Variation of the benzaldehyde substituent produced the desired quinoline derivatives in moderate to excellent yields, 55-93% (Table 14, entries 2-4).…”

“…[57] Fe(OTf)3(5mol%), solvent-free, 100°C, 3 hr 4 55 81 [75] K-10 (500mg), solvent-free, 100°C, 10 min 5 90 82 [57] Fe(OTf)3(5mol%), solvent-free, 100°C, 3 hr 6 71 88 [75] K-10(500mg), solventfree, 100°C, 10 min 7 71 83 [55] FeCl3(10mol%), toluene, 100°C, 24 hr 8 86 83 [75] K-10(500mg), solventfree, 100°C, 10 min 9 95 85 [90] (DPP)(0.1-0.5 mol eq. ), 4 min, solventfree 10 83 80 [89] Iodine (0.1 mmol), CH3NO2, r.t., 12 hr…”

“…[95] . [89] 13 C NMR (100 MHz, CDCl3): δ(ppm) 158.1 (2-C), 154.9 (6-C), 148.1 (4-C), 145.2 (8a-C), 140.0…”

Efficient One-Pot Synthesis of 1,4-Dihydropyridino[3,2-c]coumarins

“…其中吡啶并香豆素类化合物由于具有抑制 单胺氧化酶 [5] 、抗肿瘤 [6] 、止痛 [7] 、抗菌 [8] [9] (结构式 A), 二 氢喹啉并[3,2-c]香豆素 [10] (结构式 B), 具有抗肿瘤活性 的四氢喹啉并[3,2-c]香豆素 [11] (结构式 C)等, 成为香豆 素类化合物研究领域中的一个热点. 最近, 我们以稠杂环化合物为研究对象, 先后合成 了具有潜在生物活性的含吡啶 [12] 、吡喃 [13] 、呋喃 [14] 、香 豆素 [15] [17] 受到关注, 但在碘作用下的该类反应报道不 多 [18] . 另外, 在此类反应中得到相关二氢吡啶类结构的 鲜有报道 [19] .…”