Synthesis and Reaction of Novel Spiro Pyrimidine Derivatives

Abstract

2‐Mercapto‐6‐[(pyridin‐4‐ylmethylene)‐amino]‐3H‐pyrimidin‐4‐one 1 was synthesized from Schiff base reaction of 6‐amino‐2‐thiouracil with isonicotinaldehyde. The reaction of 1 with hydrazonyl chloride 2a, 2b, 2c, 2d afforded the novel pyrimidin‐4‐one 3a, 3b, 3c, 3d. Compounds 3a, 3b, 3c, 3d reacted with methyl iodide to give 4a, 4b, 4c, 4d. Subsequently, reaction of 4a, 4b, 4c, 4d with triethylamine as a catalyst in dry chloroform yielded tetraaza‐spiro[4.5]deca‐2, 8‐dien‐7‐one 5a, 5b, 5c, 5d. In addition, reaction of 1 with acrylonitrile gave pyrimidin‐propionitrile 6. The cyclization of 6 by reacting with sodium ethoxide to give pyrimido [2, 1‐b] [1,3] thiazin‐6‐one 7. The refluxing of 1 with bromine in acetic acid yielded 2‐bromo‐pyrimidin‐4‐one 8. The latter compound 8 reacted with sodium azide gave tetrazolo‐pyrimidine 10. The chemical structures of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectral analysis.

Design, Synthesis of Novel Thiourea and Pyrimidine Derivatives as Potential Antitumor Agents

“…Condensation of (11b) with acetylacetone, ethylacetoacetate and malononitrile in Zn/AcOH afforded the tetrahydropyrimidinethione derivatives (12)(13)(14), whereas the bis-acetyl derivative (15) was achieved when acetic anhydride was used (Scheme 2), according to the plausible mechanism in (Scheme 3). The 1 H NMR spectrums of (14) exhibited two triplet signals at d 1.20, 4.13 ppm for four protons in pyrimidine ring, a singlet signal 4.70 ppm for four protons of (CH 2 Moreover, the reaction of (11b) with chloroacetyl chloride in ethanol and in the presence of potassium hydroxide gave the corresponding 5-chloro-3-(4-chlorobenzyl)-6-(4-chloro-phenyl)-2-thioxo-tetrahydro-pyrimidi n-4-one (16).…”

Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

“…[2][3] Spiro heterocyclic compounds lead to the biological activity of these compounds because of the commonality of a carbon between the two rings and the lack of symmetry of these compounds due to the asymmetric nature of carbon spiro compounds. [4][5][6][7][8] Biological activities, such as promising antibacterial, antifungal, [9][10][11] anti-hyperglycemic, 12 and anti-tubercular 13 effects have been reported for spiro heterocyclic compounds.…”

MgO‐Nanoparticle‐Catalyzed Synthesis and Evaluation of Antimicrobial and Antioxidant Activity of New Multi‐Ring Compounds Containing Spiro[indoline‐3,4′‐[1,3]dithiine]

“…Biological properties have also been reported from the oxindole derivatives . Spiro's heterocyclic compound has a vital biological activity due to the presence of a carbon between the two rings and the asymmetric nature of carbon spiros . Regarding the importance of 1,3‐dithiane, indolin‐2‐one derivatives and spiro compounds in terms of biological activity, synthesis of spiro compound containing indolin‐2‐one and l,3‐dithiin is also consequential.…”