Novel and Highly Efficient Synthesis of Substituted Dibenz[b,g]1,5-oxazocines. A Direct Comparison of the Solution versus Solid-Phase Approach

✍ Scribed by Xiaohu Ouyang; Zhidong Chen; Longbin Liu; Celia Dominguez; Alexander S. Kiselyov

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 436 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00120-4

✦ Synopsis

We describe a novel and highly efficient synthesis of substituted dibenz[b,g]1,5-oxazocines. The procedure is based on the S N Ar of fluoride with the phenolic hydroxide of the properly assembled acyclic intermediate. A direct comparison of the solution-phase vs the solid-phase synthesis has been conducted. The speed of the synthesis, the purity of the desired eight-membered heterocycles (Ͼ95%), as well as the diversity of the resultant library are definite advantages of the solid-phase procedure. Yields of dibenz[b,g]1,5-oxazocines synthesized via the solid-phase approach were generally better, while the purity of the products synthesized by both methods were identical.