Efficient Access to New Chemical Space Through Flow—Construction of Druglike Macrocycles Through Copper-Surface-Catalyzed Azide–Alkyne Cycloaddition Reactions
✍ Scribed by Andrew R. Bogdan; Keith James
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 271 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
A series of 12‐ to 22‐membered macrocycles, with druglike functionality and properties, have been generated by using a simple and efficient copper‐catalyzed azide–acetylene cycloaddition reaction, conducted in flow in high‐temperature copper tubing, under environmentally friendly conditions. The triazole‐containing macrocycles have been generated in up to 90 % yield in a 5 min reaction, without resorting to the high‐dilution conditions typical of macrocyclization reactions. This approach represents a very efficient method for constructing this important class of molecules, in terms of yield, concentration, and environmental considerations.