Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles

作者：Milgram Benjamin C; Eskildsen Katrine; Richter Steven M; Scheidt W Robert; Scheidt Karl A^*

来源：Journal of Organic Chemistry, 2007, 72(10): 3941-3944.

DOI：10.1021/jo070389+

[GRAPHICS]
The synthesis of N-acyl 3,4-disubstituted pyrroles can be accomplished directly from hydrazine and an aldehyde via a Piloty-Robinson pyrrole synthesis. The use of microwave radiation for the cyclization and pyrrole formation greatly reduces the time necessary for this process and facilitates moderate to good yields from hydrazine for the corresponding 3,4-disubstituted products (5-12). By simple hydrolysis, the free N-H pyrroles can be accessed after the Piloty-Robinson reaction and then used directly in the synthesis of octaethylporphyrin (H2OEP, 14) and octaethyltetraphenylporphyrin (H2OETPP, 15).

• 出版日期2007-5-11
• 单位西北大学