A Novel One-Pot, Three-Component Synthesis of 5-Imino-2,3,5,8-tetrahydropyrazolo[1,2-a]pyridazin-1-one Derivatives

Abstract

It was found that the zwitterionic intermediate obtained from the addition of isocyanides to dimethyl acetylenedicarboxylate could react with 1,3-dipolar compounds under mild conditions to produce 5-imino-2,3,5,8-tetrahydropyrazolo[1,2-a]pyridazin-1-one derivatives in high yields. A plausible mechanism was also discussed for this process.

Key words

isocyanide - dimethyl acetylenedicarboxylate - multicomponent reactions - 1,3-dipolar compounds - 5-imino-2,3,5,8-tetrahydropyrazolo[1,2-a]pyridazin-1-one

References

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12

The atomic coordinates for 4a have been deposited at the Cambridge Crystallographic Data Centre (deposition number CCDC 702357). The coordinates can be obtained on request from the Director Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, e-mail: [e-mail], fax: [phone].

15

The atomic coordinates for 8 have been deposited at the Cambridge Crystallographic Data Centre (deposition number CCDC 713140). The coordinates can be obtained on request from the Director Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, e-mail: [e-mail], fax: [phone].