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Direct α-Imination of N-Acyl Pyrazoles with Nitrosoarenes
Chiara Volpe1, Sara Meninno1, Giulia Mirra1
1Dipartimento di Chimica e Biologia , Università di Salerno , Via Giovanni Paolo II 132 , 84084 Fisciano , Italy.
Abstract:
Unprecedented α-imino N-acyl pyrazoles were efficiently and selectively prepared through the 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed reaction of nitrosoarenes with N-acyl pyrazoles via an N-nitroso aldol reaction/dehydration sequence. The α-imino acyl pyrazoles were demonstrated to be new versatile intermediates for practical one-pot syntheses of α-imino amides, dipeptide precursors, esters, and β-amino alcohols. The synthetic method competes with known protocols in terms of ready availability of the reagents and catalyst, mild and catalytic reaction conditions, gram-scale applicability, and scope of the α-imino acid derivatives achievable.
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