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Synthesis 2005(19): 3412-3422
DOI: 10.1055/s-2005-918473
DOI: 10.1055/s-2005-918473
PAPER
© Georg Thieme Verlag Stuttgart · New York
Microwave-Assisted Synthesis of 2,5-Piperazinediones under Solvent-Free Conditions
Weitere Informationen
Received
14 September 2005
Publikationsdatum:
14. November 2005 (online)
Publikationsverlauf
Publikationsdatum:
14. November 2005 (online)
Abstract
A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters.
Key words
microwave irradiation - diketopiperazines - dipeptides - cyclizations - heterocycles
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References
Attempts to use a silica gel bath as the heat sink were unsuccessful.
22Working at these scales, it is advisable to preheat the alumina in the heat sink before introducing the vial or flask containing the dipeptide. For instance, the preparation of compound 5g starting from 1 g of the dipeptide was carried out in 97% yield after preheating the alumina bath for 5 min followed by a single 5 min pulse, while a reaction in the same scale without preheating required 18 min (in 3-min pulses) and gave 87% yield.
35In order to facilitate the comparison of NMR assignments, the numbering employed for C6-unsubstituted systems has been retained in these compounds, even though it does not assign the lowest locant to the first named substituents, all other factors being equal.