Reaction of methylene-bis [5-hydroxyfurocoumarins] with amines and hydrazines

ABSTRACT

Fusion of 6, 6'-methylene-bis-[5-hydroxybergapten] [IIIa] or [5- hydroxyisopimpinellin] [IIIb] with aromatic amines and hydrazine hydrate led to the formation of 6, 6'-methylene-bis-[5-amino] [IVa-f] or [5-hydrazino] [IVg], h] derivatives. On the other hand, when IIIa or IIIb were refluxed with aliphatic amines, cleavage of the methylene bridge followed by opening of the coumarin ring occurred to give the corresponding alpa-substituted acetamides [Va-d]. Fusion of IIIa or IIIb with phenylhydrazine also led to the methylene bridge followed by opening of the coumarin ring to form VIa, b. The reaction of 5- hydroxybergapten or 5-hydroxyisopimpinellin with propylamine or benzylamine in ethanol led to the respective 5-amino-derivatives [VIIa-c]. The antimicrobial activity of compounds IVa, b, e, f, Va, b, d and VIa, b has been tested. Only compound Vb showed a broad spectrum activity