Ethyl {4‐[2‐(saccharin‐2‐yl)acetylsulfamoyl]phenylazo}cyanoacetate in the synthesis of polyfunctionally heteroaromatic derivatives

Abstract

magnified imageAn efficient and direct one‐pot reaction of ethyl saccharinylcyanoacetate derivative 3 with a variety of active methylene reagents and nitrogen nucleophiles afforded novel series of polyfunctionally substituted heteroaromatic derivatives 5–13, respectively. The pyrazole derivative 13 was seemed to be the excellent precursors for the synthesis of pyrazolo[1,5‐a]pyrimidine derivatives 14–24. The antimicrobial screening of some synthesized products was evaluated against some selected bacteria and fungi. The structures of the synthesized derivatives were established by elemental and spectral data. J. Heterocyclic Chem., (2009).

Efficient Synthesis of Thieno[2,3-d]Pyrimidines and Related Fused Systems

“…The formed precipitate was filtered off, dried and recrystallised from dioxane to give 8.Yield, 0.55 g (86%); m.p. 186-188 °C; IR: ν = 3400-3210 (NH 2 , NH), 1678 cm −1 (CO); 1 H NMR (DMSO- 3-(Chloroacetyl)-2,5-dimethyl-6-(4-nitrophenoxy)thieno [2,3-d]pyrimidin-4-(3H)-one (17): A mixture of compound 16 (0.63 g, 2 mmol) and chloroacetyl chloride (2 mmol) in DMF (20 mL) was heated under reflux for 3 h. The reaction mixture after cooling was poured onto cold water (30 mL) and the solid precipitate obtained was filtered off and recrystallised from benzene to give 17. Yield, 0.54 g (68%); m.p.…”

“…[1][2][3][4][5][6][7][8] In addition, triazine and triazole compounds possess diverse biological uses such as antifungals, insecticides, herbicides and plant growth regulators. [9][10][11][12][13][14][15] Encouraged by these findings and as a continuation of our studies into the synthesis of a variety of heterocyclic systems of biological interest, [16][17][18] we have found that ethyl 2-aminothiophene-3-carboxylate 1 is a versatile, readily accessible building block for the synthesis of new series of fused thienopyrimidine derivatives.…”

Synthesis, Crystal Structure, and Fungicidal Activity of Novel 1,5‐Diaryl‐1H‐Pyrazol‐3‐Oxy Derivatives Containing Oxyacetic Acid or Oxy(2‐thioxothiazolidin‐3‐yl)ethanone Moieties

“…As the discovery of the strobilurin fungicide pyraclostrobin by Baden Aniline and Soda Factory (BASF) scientists, 1 H ‐pyrazol‐3‐oxy derivatives have attracted considerable attention in chemical and medicinal research because of their low mammalian toxicity and diverse bioactivities such as fungicidal , insecticidal , herbicidal , and plant growth regulatory activities . Furthermore, several biological studies have also pointed out the value of alkyloxyacetate and oxyacetic acid as bioactive groups.…”

Synthesis of New Peptidyl- and Glycosylpyrimidine Derivatives

“…19 Significant antibacterial and anticancer activities of glycosides have attracted many workers to attempt to improve the biological activity of these compounds by the glycosylation in order to increase their solubility in water and guidance quality. [20][21][22] Guided by the above observations, and in continuation of our interest in the synthesis of heterocycles of medical applications, [23][24][25] we report here a convenient synthesis of new pyrimidine derivatives conjugated with flexible amino acids and glycosyl moiety as side chains hoping that the produced compounds will have improved biological potential.…”