Abstract:The 6-aryl-1-(3-chloropropanoyl)-4-[(E)-1-(2-furyl)methylidene)]-1,2,3,4-tetrahydro-3-pyridazinones (6a-d) were synthesized by the reaction of acid chloride 3 with α-aracyl(β-2-furyl)acrylic acid hydrazides (2a-d) in a high yield, one pot reaction. On the other hand, 2-(2-chloroethyl)-5-[α-aracyl-β-(2-furyl)]-(E)-vinyl-1,3,4-oxadiazoles (7a-d) were also prepared by cyclodehydration ofhydrazine derivatives (4a-d). The proposed structures of the products were confirmed by elemental analysis, spectral data and chemical evidence.

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Novel N-{ 6 -a r y l -4 -[ (E) -2 -f u r y l m e t h y l e n e ] -1 , 2 , 3 , 4 -t e t r a h y d r o -3 -o x o p y r i d a z i n -1 -y l c a r b o n y l } -p-t o l u e n esulfonamides 4a-d were prepared by the reaction of (E)-2-aroylmethyl-3-(2-furyl) acrylohydrazides 2a-d with tosylisocyanate. This has been shown to occur by initial formation of (E)-2-aroylmethyl-3-(2-furyl)-N'-(tosylaminocarbonyl) acrylohydrazides 3a-d followed by acid catalyzed cyclization to afford N-{5-[(E)-1-aroylmethyl-2-(2-furyl)vinyl]-1,3,4-oxadiazol-2-yl}-p-toluenesulfonamides 5a-d.

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N‐[(5‐Cyano‐2‐oxoimidazolidin‐4‐yl)‐iminomethyl]‐p‐toluensulfonamide 3 was prepared in fairly good yield by the base catalyzed cyclisation of N‐[(Z)‐2‐amino‐1,2‐dicycanovinylcarbamoyl]‐p‐toluenesulfon‐amide 2. The N‐[(Z)‐2‐amino‐1,2‐dicycanovinyl carbamoyl]‐p‐toluenesulfonamide 2 was reacted readily with two molar amount of p‐nitrobenzaldehyde at room temperature in the presence of base to give 7,8‐dihy‐dro‐2‐(4‐nitrophenyl)‐8‐oxo‐9‐tosylpurine‐6‐carboxamide 8. Thiation of compounds 3 and 8 using Lawesson's reagent in tetrahydrofuran gave novel thioimidazoles 4, 5, and 6 and thiopurines 9, 10, and 11, which have been characterized spectroscopically.