A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline

A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation...

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Published in:Organic & biomolecular chemistry 2015-04, Vol.13 (15), p.4399-4403
Main Authors: Nsengiyumva, Olivier, Hamedzadeh, Sadra, McDaniel, James, Macho, Jocelyn, Simpson, Grant, Panda, Siva S, Ha, Khanh, Lebedyeva, Iryna, Faidallah, Hassan M, Al-Mohammadi, Manal Metgen, Hall, C Dennis, Katritzky, Alan R
Format: Article
Language:English
Subjects:
Animals
Biological Products - chemical synthesis
Biological Products - chemistry
Cyclization
Diketopiperazines - chemical synthesis
Diketopiperazines - chemistry
Dipeptides - chemistry
Ethylamines - chemistry
Porifera - chemistry
Proline - analogs & derivatives
Proline - chemical synthesis
Stereoisomerism
Triazoles - chemistry
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Summary:A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00023h