Catalyst- and Base-Free Synthesis of Morita-Baylis-Hillman and Rauhut-Currier Adducts of β-Aminonitroalkenes
Snehal Pednekar1, Sudheesh T Sivanandan1, Deepak Kumar1
1Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India.
Abstract:
A facile, base- and catalyst-free synthesis of Morita-Baylis-Hillman and Rauhut-Currier adducts of β-aminonitroalkenes with different electrophiles such as ethyl glyoxylate, trifluoropyruvate, ninhydrin, vinyl sulfone, and N-tosylazadiene is reported. The products are formed in good to excellent yields at room temperature with a broad substrate scope. The adducts of ninhydrin and β-aminonitroalkene spontaneously cyclize to fused indenopyrroles. Gram-scale reactions and synthetic transformations of the adducts are also reported here.
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