Collect. Czech. Chem. Commun. 1990, 55, 540-545

N-substituted tricyclic isoquinoline hydantoins

Ioannis Niopas and Gordon A. Smail

Department of Pharmacy, University of Strathclyde, Glasgow, G1 1XW, U.K.


Mannich condensation of the 1,3-dioxo-5H-10,10a-dihydroimidazo[1,5-b]isoquinoline (Ia) and 5-ethoxy-10-bromo-1,3-dioxo-5H-imidazo[1,5-b]isoquinoline (IVa) with secondary amines gave a series of N-2-aminomethyl isoquinoline hydantoins IIa-IIg and IVb, respectively. Alkylation of Ia with N,N-dialkylaminoethyl chlorides and ethyl chloroacetate afforded the N-dialkylaminoethyl and N-ethoxycarbonylmethyl derivatives Va, Vb and IIh. The N-2-hydroxymethyl and N-2-amino isoquinoline hydantoins IIj and If were also prepared.