Reactivity of 2-Ethoxyquinazolin- 4-yl hydrazine and its Use in Synthesis of Novel Quinazoline Derivatives of Antimicrobial Activity

  •  Maher El-Hashash    
  •  Khalid Darwish    
  •  Sameh Rizk    
  •  Fakhry El-Bassiouny    


[Abstract]   The reactions of 2-ethoxy-4-hydrazinoquinazoline 2  with diethyl oxalate and ethyl chloroacetate gave 6-ethoxy-2H-[1,2,4]triazino[4,3-c]quinazoline-3,4-dione 3 and 6-ethoxy-2,3-dihydro-4H-[1,2,4]triazino[4,3-c]quinazolin-4-one 4 respectively.  A series of 5-ethoxy-2-X-[1,2,4]triazolo[1, 5-c]quinazolines  5a-d  was also produced  by reacting 2 with the acid chlorides namely: benzoyl, crotonyl, cinnamyl and 2-furoyl chlorides via Dimroth rearrangement. Also, 2 reacted  with ethyl chloroformate giving   6. Condensation of 2 with acetone gave Schiff  base 7, and with monosaccharides  gave the  sugar hydrazones 8a-e  which were thereafter acetylated  giving the corresponding 9a-e.  Cyclization  of  8a-e by iron(III) chloride gave triazoloquinazolines 10a-e acyclic  C-nucleosides which, by acetylation, afforded  11a-e.  All products were confirmed by elemental,  IR, MS, and 1H-NMR analysis.   Products 8-11 were chosen for biological screening test against gram(+ ive) and gram(- ive) bacteria.

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