Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines

The regioselective addition of Grignard reagents to mono- and disubstituted N-acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45–100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ(5)-2-oxopiperazine...

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Autores principales: St. Hilaire, Valentine R, Hopkins, William E, Miller, Yenteeo S, Dandepally, Srinivasa R, Williams, Alfred L
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6334805/
https://www.ncbi.nlm.nih.gov/pubmed/30680041
http://dx.doi.org/10.3762/bjoc.15.8
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author St. Hilaire, Valentine R
Hopkins, William E
Miller, Yenteeo S
Dandepally, Srinivasa R
Williams, Alfred L
author_facet St. Hilaire, Valentine R
Hopkins, William E
Miller, Yenteeo S
Dandepally, Srinivasa R
Williams, Alfred L
author_sort St. Hilaire, Valentine R
collection PubMed
description The regioselective addition of Grignard reagents to mono- and disubstituted N-acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45–100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ(5)-2-oxopiperazines providing a simple and efficient approach towards their preparation.
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spelling pubmed-63348052019-01-24 Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines St. Hilaire, Valentine R Hopkins, William E Miller, Yenteeo S Dandepally, Srinivasa R Williams, Alfred L Beilstein J Org Chem Full Research Paper The regioselective addition of Grignard reagents to mono- and disubstituted N-acylpyrazinium salts affording substituted 1,2-dihydropyrazines in modest to excellent yields (45–100%) is described. Under acidic conditions, these 1,2-dihydropyrazines can be converted to substituted Δ(5)-2-oxopiperazines providing a simple and efficient approach towards their preparation. Beilstein-Institut 2019-01-08 /pmc/articles/PMC6334805/ /pubmed/30680041 http://dx.doi.org/10.3762/bjoc.15.8 Text en Copyright © 2019, St. Hilaire et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
St. Hilaire, Valentine R
Hopkins, William E
Miller, Yenteeo S
Dandepally, Srinivasa R
Williams, Alfred L
Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
title Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
title_full Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
title_fullStr Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
title_full_unstemmed Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
title_short Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
title_sort regioselective addition of grignard reagents to n-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and δ(5)-2-oxopiperazines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6334805/
https://www.ncbi.nlm.nih.gov/pubmed/30680041
http://dx.doi.org/10.3762/bjoc.15.8
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