Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 10, Pages 3941-3944Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo070389+
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- NIGMS NIH HHS [GM 38401, R01 GM038401-34, R01 GM038401-33, R01 GM038401] Funding Source: Medline
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[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).
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