CuSO₄-Glucose for in Situ Generation of Controlled Cu(I)-Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehyde with Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles

Sankar K. Guchhait*, Ajay L. Chandgude and Garima Priyadarshani

*Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), S. A. S. Nagar (Mohali), 160062, Punjab, India, Email: skguchhaitniper.ac.in

S. K. Guchhait, A. L. Chandgude, G. Priyadarshani, J. Org. Chem., 2012, 77, 4438-4444.

DOI: 10.1021/jo3003024

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Abstract

With a mixed Cu(I)-Cu(II) system in situ generated by partial reduction of CuSO₄ with glucose, an efficient and eco-friendly multicomponent cascade reaction of A³-coupling of heterocyclic amidine with aldehyde and alkyne, 5-exo-dig cycloisomerization, and prototropic shift has afforded therapeutically important versatile N-fused imidazoles.

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Key Words

imidazo[1,2-a]pyridines, multicomponent reactions, green chemistry

ID: J42-Y2012-1320

CuSO4-Glucose for in Situ Generation of Controlled Cu(I)-Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehyde with Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles

Sankar K. Guchhait*, Ajay L. Chandgude and Garima Priyadarshani

CuSO₄-Glucose for in Situ Generation of Controlled Cu(I)-Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehyde with Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles