Future Medicinal Chemistry 2010-02-01

Microwave synthesis of cucurbit[n]urils.

Nial J Wheate, Nilesh Patel, Oliver B Sutcliffe

Index: Future Med. Chem. 2(2) , 231-6, (2010)

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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 H(2)SO(4) 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.