Synthesis of 5-Phenyl 2-Functionalized Pyrroles by Amino Heck and Tandem Amino Heck Carbonylation Reactions

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doi:10.1071/CH07132

Synthesis of 5-Phenyl 2-Functionalized Pyrroles by Amino Heck and Tandem Amino Heck Carbonylation Reactions

Shazia Zaman ^A ^B ^D, Mitsuru Kitamura ^B ^C, Andrew D. Abell ^A

^A Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
^B Department of Chemistry, Graduate School of Science, 7-3-1 Hongo, Bunkyo-Ku Tokyo 113-0033, Japan.
^C Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan.
^D Corresponding author. Email: shazia.zaman@canterbury.ac.nz





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Australian Journal of Chemistry 60(8) 624–626 http://dx.doi.org/10.1071/CH07132
Submitted: 30 April 2007 Accepted: 20 June 2007 Published online: 9 August 2007

Abstract

2-Methyl-, 2-(methoxycarbonyl)methyl-, and 2,2-[(ethoxycarbonyl)(methoxycarbonyl)]methyl-5-phenylpyrroles are prepared from the corresponding 3-butynyl and 4-(methoxycarbonyl)-3-butynyl phenyl ketone O-pentafluorobenzoyl oximes by amino Heck cyclization and tandem amino Heck carbonylation, respectively.