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

Benjamin C. Milgram; Katrine Eskildsen; Steven M. Richter; W. Robert Scheidt; Karl A. Scheidt

doi:10.1021/jo070389+

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

Benjamin C. Milgram, Katrine Eskildsen, Steven M. Richter, W. Robert Scheidt, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

Abstract

(Chemical Equation Presented) 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).

Original language	English (US)
Pages (from-to)	3941-3944
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	10
DOIs	https://doi.org/10.1021/jo070389+
State	Published - May 11 2007

ASJC Scopus subject areas

Organic Chemistry

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

abstract = "(Chemical Equation Presented) 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).",

author = "Milgram, {Benjamin C.} and Katrine Eskildsen and Richter, {Steven M.} and Scheidt, {W. Robert} and Scheidt, {Karl A.}",

year = "2007",

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doi = "10.1021/jo070389+",

language = "English (US)",

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T1 - Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles

AU - Milgram, Benjamin C.

AU - Eskildsen, Katrine

AU - Richter, Steven M.

AU - Scheidt, W. Robert

AU - Scheidt, Karl A.

PY - 2007/5/11

Y1 - 2007/5/11

N2 - (Chemical Equation Presented) 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).

AB - (Chemical Equation Presented) 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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