Two-step one-pot synthesis of dihydropyrazinones as Xaa-Ser dipeptide isosteres through morpholine acetal rearrangement-Reference-Cited by-同舟云学术

Two-step one-pot synthesis of dihydropyrazinones as Xaa-Ser dipeptide isosteres through morpholine acetal rearrangement

Published:2015 Issue:25 Volume:13 Page:7013-7019
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Lenci Elena¹²³⁴,Innocenti Riccardo¹²³⁴,Menchi Gloria¹²³⁴⁵,Faggi Cristina¹²³⁴,Trabocchi Andrea¹²³⁴⁵

Affiliation:

1. Department of Chemistry “Ugo Schiff”

2. University of Florence

3. Sesto Fiorentino, Florence

4. Italy

5. Interdepartmental Center for Preclinical Development of Molecular Imaging (CISPIM)

Abstract

The synthesis of the uncommon dihydropyrazinone ring was accomplished by taking advantage of the ring rearrangement ofN-acylated morpholine acetal derived from serine under acidic treatment and in the presence of 2,6-lutidine, resulting in a constrained Xaa-Ser dipeptide isostere.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2015/OB/C5OB00783F

Reference27 articles.

1. Design and Synthesis of Novel Bioactive Peptides and Peptidomimetics

2. LACTAM RESTRICTION OF PEPTIDE CONFORMATION IN CYCLIC HEXAPEPTIDES WHICH ALTER RUMEN FERMENTATION

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