Studies on Isocyanides and Related Compounds; A Facile Synthesis of Functionalized 3(2H)-Pyridazinones via Ugi Four-Component Condensation

Abstract

The reaction between diarylglyoxal monohydrazones 1, isocyanides 2, aldehydes 3a-c, and methylene active acids 4 afforded a series of 3(2H)-pyridazinones 5 in a very simple manner. The intermediate Ugi four-component condensation products were never observed because of their tendency to cyclize. When the less reactive cyclopentanone (3d) is used instead of aldehydes 3a-c, satisfactory yields of 3(2H)-pyridazinones 7 were obtained by employing the pre-formed azine 8.

heterocycles - hydrazones - Knoevenagel condensation - isocyanides - condensation - Ugi reaction

References

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<A NAME="RT00802SS-10">10</A>

The singlet signals of the methyl groups and the multiplet signal of H-1 of the cyclohexane ring are overlapped.

<A NAME="RT00802SS-11">11</A>

After repeated recrystallizations we were unable to obtain satisfactory analytical data for this compound.