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  • Title: Synthesis with nitriles: synthesis of some new mercaptopyridazine, mercaptopyridazino[1,6-a]quinazoline and thiophene derivatives.
    Author: Al-Sheikh MA.
    Journal: Molecules; 2008; 13(11):2750-7. PubMed ID: 18985952.
    Abstract:
    2-(1-(4-Bromophenyl)-2-thiocyanatoethylidene)malononitrile (3) undergoes azo coupling with diazotized aromatic amines to afford arylhydrazone derivatives, which are readily cyclized to afford the corresponding 3(2H)-pyridazinimine derivatives upon reflux in aqueous NaOH. Under similar condition an o-cyanoarylhydrazone derivative was cyclized into 6H-pyridazino[1,6-a]quinazolin-6-imine, which in turn was easily transformed into 6H-pyridazino[1,6-a]quinazolin-6-one on reflux in ethanolic/HCl. Compound 3 afforded substituted 5-acetylthiophene derivatives upon reflux in AcOH/HCl mixtures.
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