Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

H. Surya Prakash Rao; S. Jothilingam; Hans W. Scheeren

doi:10.1016/j.tet.2003.11.087

Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

H. Surya Prakash Rao, S. Jothilingam, Hans W. Scheeren

Precision Radio-Theranostics Translational Laboratories (PRT2L)

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

91 Scopus citations

Abstract

Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement.

Original language	English
Pages (from-to)	1625-1630
Number of pages	6
Journal	Tetrahedron
Volume	60
Issue number	7
DOIs	https://doi.org/10.1016/j.tet.2003.11.087
State	Published - Feb 9 2004

Keywords

Alkyl and aryl ammonium formates
Amination-cyclization
Microwave assisted organic synthesis
Pyrrole synthesis
Reduction

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10.1016/j.tet.2003.11.087

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title = "Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones",

abstract = "Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement.",

keywords = "Alkyl and aryl ammonium formates, Amination-cyclization, Microwave assisted organic synthesis, Pyrrole synthesis, Reduction",

author = "Rao, {H. Surya Prakash} and S. Jothilingam and Scheeren, {Hans W.}",

note = "Funding Information: S. J. thanks CSIR for a fellowship. H. S. P. R. thanks the UGC-SAP program and CSIR, India, for financial support. We thank Professor A. Srikrishna, for spectra and helpful discussions. We also thank RSIC, IITM, Chennai and SIF, IISc, Bangalore, for recording the spectra.",

year = "2004",

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day = "9",

doi = "10.1016/j.tet.2003.11.087",

language = "English",

volume = "60",

pages = "1625--1630",

journal = "Tetrahedron",

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TY - JOUR

T1 - Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

AU - Rao, H. Surya Prakash

AU - Jothilingam, S.

AU - Scheeren, Hans W.

N1 - Funding Information: S. J. thanks CSIR for a fellowship. H. S. P. R. thanks the UGC-SAP program and CSIR, India, for financial support. We thank Professor A. Srikrishna, for spectra and helpful discussions. We also thank RSIC, IITM, Chennai and SIF, IISc, Bangalore, for recording the spectra.

PY - 2004/2/9

Y1 - 2004/2/9

N2 - Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement.

AB - Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement.

KW - Alkyl and aryl ammonium formates

KW - Amination-cyclization

KW - Microwave assisted organic synthesis

KW - Pyrrole synthesis

KW - Reduction

UR - http://www.scopus.com/inward/record.url?scp=0742306820&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2003.11.087

DO - 10.1016/j.tet.2003.11.087

M3 - Article

AN - SCOPUS:0742306820

SN - 0040-4020

VL - 60

SP - 1625

EP - 1630

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

Abstract

Keywords

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