Simple One‐Pot Three‐Component Synthesis of 2‐Oxo‐1,11b‐dihydro‐2H‐pyrimido[2,1‐a]isoquinolines.

Abstract

Fused pyrimidine derivativesFused pyrimidine derivatives R 0515 Simple One-Pot Three-Component Synthesis of 2-Oxo-1,11b-dihydro-2H-pyrimido[2,1-a]isoquinolines. -(ADIB*, M.; MOLLAHOSSEINI, M.; YAVARI, H.; SAYAHI, M. H.; BIJANZADEH, H. R.; Synthesis 2004, 6, 861-864; Dep. Chem., Fac. Sci., Tehran Univ., Tehran, Iran; Eng.) -C. Herrmann

Cyanoacetylenes as Triggers and Partners in KOH-Assisted Assemblies of Quinoline-Based Dihydropyrimido[1,2-a]quinolin-3-ones on Water

“…NMR spectra were recorded on a Bruker DPX-400 spectrometer (400.13 MHz for 1 H and 100.62 MHz for 13 C) in DMSO-d 6 and CDCl 3 . Internal standards were HMDS (for 1 H nuclei δ 0.05 ppm) or residual solvent signals (for 13 C nuclei δ 77.16 ppm). The resonance signals of carbon atoms were assigned based on 1 H− 13 C HSQC and 1 H− 13 C HMBC experiments.…”

“…1 H NMR (400. 13 Also, side 2-phenylquinoline-3-carbonitrile (4a) (6 mg, 5%) was isolated as white powder, mp 197−198 °C (EtOH). 22a 1 H NMR and IR spectra are similar to the literature data.…”

“…IR (microlayer): 1607, 1657 3 J 9,10 = 7.9 Hz, 1H, H-10), 6.13 (s, 1H, H-2), 5.89 (dd, 3 J 5,6 = 9.6 Hz, 3 J 4a,5 = 4.8 Hz, 1H, H-5), 5.75−5.73 (m, 1H, H-4a), 1.23 (s, 3H, Me) ppm. 13 1-(4-Ethylphenyl)-4,4a-dihydro-3H-pyrimido[1,2-a]quinolin-3one (3c). Method B.…”

“…1 H NMR (400.13 MHz, CDCl 3 ): δ 7.53−7.51 (m, 2H, H 2′,6′ from Ar), 7.22−7.20 (m, 2H, H 3′,5′ from Ar), 7.05 (d, 3 J 7,8 = 9.0 Hz, 1H, H-7), 6.84−6.76 (m, 3H, H-6, H-8, H-9), 6.22 (d, 3 J 9,10 = 8.0 Hz, 1H, H-10), 6.15 (s, 1H, H-2), 6.04 (br s, 1H, NH), 5.86 (dd, 3 J 5,6 = 9.8 Hz, 3 J 4a,5 = 4.6 Hz, 1H, H-5), 5.76−5.74 (m, 1H, H-4a), 2.66 (q, 3 J H,H = 7.6 Hz, 2H, CH 2 from Et), 1.23 (t, 3H, Me from Et) ppm. 13 C{ 1 H} NMR (100.62 MHz, CDCl 3 ): δ 164.8 (C-3), 153.9 (C-1), 147.6 (C 4′ from Ar), 137.7 (C-10a), 131.9 (C 1′ from Ar), 130.2 (C-6), 129.3 (C-9), 128.9 (C 3′,5′ from Ar), 127.9 (C-7), 127. 4-(3-Oxo-4,4a-dihydro-3H-pyrimido[1,2-a]quinolin-1-yl)benzonitrile (3e).…”

“…In this context, the representatives of pyrimidoquinolinones were reported to possess antiplatelet activity. 12 At present, dihydropyrimido[1,2-a]quinolin-3-ones, still limited in number, are assembled from (i) quinoline, DMAD, and arylisocyanate (only one example, the reaction proceeds in CH 2 Cl 2 , which is toxic and cancerogenic and arylisocyanates are lacrimators); 13 (ii) 3-(5,5-dimethyl-3oxocyclohex-1-enylamino)carboxylic acids and aldehydes with malononitrile (or unsaturated dinitriles); 14−16 (iii) 5-oxo-2,5dihydroisoxazole-4-carboxylate and 2-chloroquinolines. 17 One rapidly developing trend in modern organic chemistry is so-termed "on-water" synthesis.…”