Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media

doi:10.3390/molecules14082836

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Molecules 2009, 14(8), 2836-2849; doi:10.3390/molecules14082836

Article

Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media

Lemuel Pérez-Picaso¹, Jaime Escalante¹, Horacio F. Olivo² and María Yolanda Rios^1,*

¹ Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, México ² Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, IA 52242, USA

* Author to whom correspondence should be addressed.

Received: 23 June 2009; in revised form: 21 July 2009 / Accepted: 23 July 2009 / Published: 31 July 2009

(This article belongs to the Special Issue Microwave Assisted Synthesis)

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Abstract: Aqueous in situ one-pot N-Boc-deprotection-cyclization of Nα-Boc-dipeptidyl-tert-butyl and methyl esters under microwave irradiation afforded 2,5-diketopiperazines (DKPs) in excellent yields. This protocol is rapid, safe, environmentally friendly, and highly efficient, and showed that the tert-butoxy moiety is also an excellent leaving group for these cyclizations.

Keywords: 2; 5-diketopiperazines; DKPs; cyclic dipeptides; microwave irradiation

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Cite This Article

MDPI and ACS Style

Pérez-Picaso, L.; Escalante, J.; Olivo, H.F.; Rios, M.Y. Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media. Molecules 2009, 14, 2836-2849.

AMA Style

Pérez-Picaso L, Escalante J, Olivo HF, Rios MY. Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media. Molecules. 2009; 14(8):2836-2849.

Chicago/Turabian Style

Pérez-Picaso, Lemuel; Escalante, Jaime; Olivo, Horacio F.; Rios, María Yolanda. 2009. "Efficient Microwave Assisted Syntheses of 2,5-Diketopiperazines in Aqueous Media." Molecules 14, no. 8: 2836-2849.

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