Cyanoacetanilide intermediates in heterocyclic synthesis. Part 7: preparation of some spiro[indoline-3,4′-pyridine] and chromeno[3,4-c]pyridine derivatives

Abstract

The reaction of cyanoacetanilide derivative 1 with some electrophiles was investigated. Treatment of compound 1 with 2-(2-oxoindol-3-ylidene)malononitrile (2a) under reflux in ethanol in the presence of piperidine afforded the spiro[indoline-3,4′-pyridine] derivative 3. Under similar conditions, condensation of compound 1 with the analog 2b yielded a spiroindole 4. Chromeno[3,4-c]pyridine derivative 6 was obtained by cyclization of chromene derivative 5 with ethyl cyanoacetate. In a similar manner, condensation of compound 5 with cylcohexanone under reflux in ethanol in the presence of sodium acetate furnished chromeno[3,4-c]quinoline derivative 7. Compound 1 was condensed with 2-hydroxy-1-naphthaldehyde to yield the benzo[f]chromeno derivative 8. Refluxing of benzochromene derivative 8 with ethyl cyanoacetate in ethanol in the presence of catalytic amount of piperidine produced benzo[f]chromeno[3,4-c]pyridine derivative 9. The structures of the newly synthesized compounds were confirmed on the basis of analytical and spectral data.

Sulfaguanidine Hybrid with Some New Pyridine-2-One Derivatives: Design, Synthesis, and Antimicrobial Activity against Multidrug-Resistant Bacteria as Dual DNA Gyrase and DHFR Inhibitors

“…Activation of T lymphocytes, natural killer, and macrophage cells mainly produce the cytokines that have immunomodulatory potential and plays a vital role in the immune response process by assisting the expulsion of abnormal cells [ 50 ]. In view of the above observations and in continuation of our program on the medicinal chemistry that demonstrated biological activity [ 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]. We report herein the synthesis of the versatile hitherto unknown 2-pyridone and chromeno-[3,4-c] pyridine derivatives containing the sulfaguanidine moiety in a single molecular framework; the rational study design is presented in Figure 1 .…”

“…Antibiotics 2021, 10, x FOR PEER REVIEW 3 of 31 the expulsion of abnormal cells [50]. In view of the above observations and in continuation of our program on the medicinal chemistry that demonstrated biological activity [51][52][53][54][55][56][57][58][59][60].…”

Enantioselective Chromatographic Separation and Lipase Catalyzed Asymmetric Resolution of Biologically Important Chiral Amines

“…Cyanoacetamide is a key moiety in synthetic chemistry and it has a wide range of application prospects [18][19][20][21][22]. It represents a crucial intermediate of fine chemical industry such as medicine, agrochemicals, and dyes [21,23].…”

“…As a polyfunctional synthon with both electrophilic (C-3, C-1) and nucleophilic (N, C-2) reactive sites (Figure 2) [21], cyanoacetamides have been customized to prepare diverse heterocyclic moieties [21,22,27,28] with different ring sizes (Figure 2), such as azirine [29], pyrrole [30], thiophene [31,32], pyrazole [33], isothiazole [34], imidazole [35], thiazole [36], thiadiazole [37], pyridine [38], pyridinone [39], pyrane [40], pyridazine [41], pyrimidine [28], thiazine [42], and triazine [36]. As a polyfunctional synthon with both electrophilic (C-3, C-1) and nucleophilic (N, C-2) reactive sites (Figure 2) [21], cyanoacetamides have been customized to prepare diverse heterocyclic moieties [21,22,27,28] with different ring sizes (Figure 2), such as azirine [29], pyrrole [30], thiophene [31,32], pyrazole [33], isothiazole [34], imidazole [35], thiazole [36], thiadiazole [37], pyridine [38], pyridinone [39], pyrane [40], pyridazine [4...…”

Synthesis of Novel 4-Thiazolidinones Linked by an Aryl Spacer to a 1,2,4-Triazine Moiety

“…On the other hand, 1,2,4-triazine derivatives are known to possess antitubercular, 19 antibacterial, 20 fungicidal, 21 insecticidal, 22 herbicidal hypotensive, and hypothermic activities. [19][20][21][22][23] In view of this and in continuation of our work on the synthesis of new heterocyclic derivatives, [24][25][26][27][28][29][30][31][32] it was thought of interest to accommodate 1,2,4-triazines and thiazolidin-4-one moieties in a single molecular framework in order to obtain new heterocyclic compounds with potential biological activity. In the present study, we explore the synthesis of hybrid heterocycles comprising 1,2,4-triazine and 4-thiazolidinone substructures.…”