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

Carlos F. Marcos; Stefano Marcaccini; Roberto Pepino; Cecilia Polo; Tomás Torroba

doi:10.1055/s-2003-38071

PAPER

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

Carlos F. Marcos^a, Stefano Marcaccini*^b, Roberto Pepino^b, Cecilia Polo^a, Tomás Torroba^c
^a Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain
^b Dipartimento di Chimica Organica ‘Ugo Schiff’, Università di Firenze, via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy
e-Mail: stefano.marcaccini@unifi.it;
^c Departamento de Química, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain

Abstract

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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.

Key words

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

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References

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

11

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