Microwave synthesis of curcurbit[n]urils

Wheate, N.J. and Patel, Nilesh and Sutcliffe, O.B. (2010) Microwave synthesis of curcurbit[n]urils. Future Medicinal Chemistry, 2 (2). pp. 231-236. ISSN 1756-8919

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Abstract

Cucurbit[n]urils (CB[n]; n = 5, 6, 7, 8 or 10) are a family of macrocycles made from the acid-catalyzed condensation of glycoluril and formaldehyde. The synthesis of CB[n] using microwave radiation has been examined and the effect of acid type, reaction time and temperature on the distribution of products has been determined. Synthesis in HCl yields CB[5], CB[6], CB[7] and CB[8] in 10 min and is most efficient at 160°C. Synthesis in H2SO4 yields mostly CB[6] in 3 min and is most efficient at 160°C. Microwave synthesis provides an efficient and cost-effective method for the large-scale production of CB[n] for a range of applications, particularly drug delivery.