The condensation reaction of 6-acetyl-3-amino-5-aryl-2-phenyl-2,5-dihydropyridazine-4-carbonitrile with triethyl orthoformate and then with hydrazine hydrate to obtain the new fused bicyclic 4-aryl-5-hydrazinyl-3-(1-hydrazonoethyl)-1-phenyl-1,4-dihydropyrimido[4,5-c]pyridazines via the Dimroth rearrangement is reported. Further cyclisation was achieved by the treatment of latter compounds with triethyl orthoformate to afford several derivatives of a novel tetracyclic fused system [1,2,4] triazolo[4″,3″:1′,6′]pyrimido[4′,5′:3,4]pyridazino[1,6-d][1,2,4]triazine.
CoburnR.A., and CarapellottiR. A., J. Pharm. Sci., 1976, 65, 1505.
9.
OdaH., MasakiY., and NagashimaH., Ann. Proc. Gifu Pharm. Univ., 1987, 36, 42.
10.
SatoY., ShimojiY., FujitaH., NishinoH., MizunoH., KobayashiS., and KamakuraS., J. Med. Chem., 1980, 23, 927.
11.
KurasawaY., NagaharaK., and TakadaA., Chem. Pharm. Bull., 1979, 27, 2143.
12.
KosaryJ., KasztreinerE., and SotiM., Heterocycles, 1983, 20, 749.
13.
NishigakiS., IchibaM., and SengaK., J. Org. Chem., 1983, 48, 1628.
14.
MoneamM.I. A., Monat. Chem., 2004, 135, 45.
15.
BakavoliM., BagherzadehG., VaseghifarM., ShiriA., PordelM., MashreghiM., PordeliP., and AraghiM., Eur. J. Med. Chem., 2010, 45, 647.
16.
RahimizadehM., ShiriA., RanaeiM., and BakavoliM., Heterocycl. Commun., 2012, 18, 39.
17.
BakavoliM., SeyediS. M., ShiriA., SaberiS., GholamiM., and SadeghianH., J. Chem. Res., 2013, 36, 48.
18.
FurnissB.S., HannafordA. J., SmithP. W. G., and TatchellA. R., Vogel's textbook of practical organic chemistry, 5th edn.Longman Scientific & Technical, London, 1989, pp. 920–953.
19.
WangS., RenZ., CaoW., and TongW., Synth. Commun., 2001, 31, 673.
20.
Al-AwadiN.A., IbrahimM. R., Al-EtaibiA. M., and ElnagdiM. H., Arkivoc, 2011, 2, 310.