Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 2, 1999, Pages 107-110

  Caldarelli, Marina ^a   Habermann, Jörg ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748719848     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809345h     Document Type: Article

References (31)

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23. Prepared by filtering an aqueous solution of potassium permanganate through Amberlyst A-27, subsequent washing of the obtained brick-red material with water and acetone and drying of the beads in vacuo.
24. The utilisation of Amberlyst A-21 for a similar reaction has been described (G. Rosini, R. Ballini and M. Petrini, Synthesis, 1986, 46), but this ion exchange resin proved to be not very efficient in our hands. Instead of Amberlite IRA-420 (OH-form), DOWEX-1 (OH-form) can be used.
25. Without an excess or in absence of the nitromethylene compound Amberlite IRA-420 (OH-form) can effect a Cannizzaro reaction of electron-poor benzaldehydes. In combination with a solid supported oxidant to reoxidise the benzylic alcohols to the aldehydes, this reaction can be used to generate benzoic acids.
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27. A related approach towards pyrroles utilising α,β-unsaturated sulfones in a classical solution phase synthesis has been described recently (Y. Abel, E. Haake, G. Haake, W. Schmidt, D. Struve, A. Walter and F.-P. Montforts, Helv. Chim. Acta, 1998, 81, 1978). This method can easily be adopted to our solid phase approach.
28. -1 and purchased from Fluka. In the reaction 1.1 equiv. of the isocyanide and 2 equiv. of the base were used.
29. -1 and purchased from Fluka. In the reaction 5 equiv. of the alkyl halide and 20 equiv. of the base were used.
30. W. Xu, R. Mohan and M. M. Morrissey, Bioorg. Med. Chem. Lett., 1998, 8, 1089. The benzylation and the allylation of the pyrrole system was not sufficiently fast enough to compete with the attack on the pyridine moiety, which led to substantial side reactions in these two cases.
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