Selective One-Pot Cascade Synthesis of N-Substituted Highly Functionalized Pyrroles from Unprotected Sugars, Primary
Xia Mengxin1, Mallikharjuna Rao Lambu1, Zaher M A Judeh1
1School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, Singapore 637459, Singapore.
Abstract:
A one-pot, three-component cascade reaction between unprotected sugars, primary amines, and 3-oxoacetonitriles gave N-substituted 2,3,5-functionalized pyrroles or N-substituted 2,3,4-functionalized pyrroles in excellent yields and selectivities. The selectivity of the reaction was achieved by simple control of the sequence of substrate addition. The reaction showed a wide substrate scope, and various types of sugars, primary amines, and oxoacetonitriles reacted smoothly. The work demonstrates a highly desired simple reaction for embedding nitrogen into sugars to produce valuable N-heterocyclic compounds that are amenable to further modifications to natural products and drug intermediates.
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