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Cyclization of thiosemicarbazide derivative: As a source of novel synthesis of some azoles and azines

Abd El‐Azim, Mohamed H. M. ; Assy, Mohamed G. ; Khalil, Mohammed I. ; Selim, Yasser A.

Journal of heterocyclic chemistry, 2020-08, Vol.57 (8), p.3153-3160 [Periódico revisado por pares]

Chichester, UK: John Wiley & Sons, Inc

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  • Título:
    Cyclization of thiosemicarbazide derivative: As a source of novel synthesis of some azoles and azines
  • Autor: Abd El‐Azim, Mohamed H. M. ; Assy, Mohamed G. ; Khalil, Mohammed I. ; Selim, Yasser A.
  • Assuntos: Acetone ; Acylation ; Azines ; Cyclohexanone ; Heterocyclic compounds ; Hydrazines ; Maleic anhydride ; Pyrazole ; Succinic acid ; Thiosemicarbazides ; Triazoles
  • É parte de: Journal of heterocyclic chemistry, 2020-08, Vol.57 (8), p.3153-3160
  • Descrição: In our study, we aimed to synthesize novel, some biologically active compounds, Azoles and Azines derivatives, that to be nitrogen‐containing heterocycles, and have their diverse therapeutic values. Thiosemicarbazide, 2, was obtained from the attack of nitrogen of hydrazine to the carbon of heteroallene function of compound 1. Triazolotriazole derivative, 4, was obtained from the reaction of 2 with diethyl malonate. Cyclization of thiourea unit of compound 2 with heteroallene, 1, gave trazine, 6. Benzolyation of 2 using benzoyl chloride formed triazole derivative, 8. Reaction of 2 and maleic anhydride gave furothiadazine, 10. Cyclohexanopyrimidinthione, 12, was obtained from cyclocondensation of cyclohexanone with 2. Triazole, 14, was obtained from 2 and ammonium isothiocynate under thermal condition. Reaction of 2 with ethyl bromoacetate gave thiazole derivative, 16. [2+3] Cyclocondensation of acetyl acetone with 2 provided pyrazole, 18. Triazolotriazole, 20, was obtained from formalin and 2. Compound 2 suffers intramolecular base mediated cyclization affording pyrazole, 21. Keeping 2 and propinaldehyde under reflux provided triazolotriazole, 24. Acylation of 2 by succinic acid formed pyridazine derivative, 27.
  • Editor: Chichester, UK: John Wiley & Sons, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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