Solid phase synthesis of aryl and heteroaryl amines using the Curtius rearrangement

✍ Scribed by Satoshi Sunami; Takeshi Sagara; Mitsuru Ohkubo; Hajime Morishima

• Book ID: 104260834
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 190 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00036-2

✦ Synopsis

An efficient method for the solid phase synthesis of secondary ary| amines and heteroaryl amines was developed. The key step was the formation of aryl or heteroaryl carbamates using the Curtius rearrangement of aryl carboxylic acids with Wang resin as a trapping hydroxyl group. N-alkylation reactions of resin-bound carbamates under the Mitsunobu condition or using sodium hydride gave secondary aryl or heteroaryl amines in good yields. The developed method can be applied in the preparation of libraries