Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

An efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual pro...

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Autores principales: Ievlev, Mikhail Yu, Ershov, Oleg V, Belikov, Mikhail Yu, Milovidova, Angelina G, Tafeenko, Viktor A, Nasakin, Oleg E
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082461/
https://www.ncbi.nlm.nih.gov/pubmed/27829915
http://dx.doi.org/10.3762/bjoc.12.198
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author Ievlev, Mikhail Yu
Ershov, Oleg V
Belikov, Mikhail Yu
Milovidova, Angelina G
Tafeenko, Viktor A
Nasakin, Oleg E
author_facet Ievlev, Mikhail Yu
Ershov, Oleg V
Belikov, Mikhail Yu
Milovidova, Angelina G
Tafeenko, Viktor A
Nasakin, Oleg E
author_sort Ievlev, Mikhail Yu
collection PubMed
description An efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation.
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spelling pubmed-50824612016-11-09 Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group Ievlev, Mikhail Yu Ershov, Oleg V Belikov, Mikhail Yu Milovidova, Angelina G Tafeenko, Viktor A Nasakin, Oleg E Beilstein J Org Chem Full Research Paper An efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation. Beilstein-Institut 2016-09-27 /pmc/articles/PMC5082461/ /pubmed/27829915 http://dx.doi.org/10.3762/bjoc.12.198 Text en Copyright © 2016, Ievlev 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), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Ievlev, Mikhail Yu
Ershov, Oleg V
Belikov, Mikhail Yu
Milovidova, Angelina G
Tafeenko, Viktor A
Nasakin, Oleg E
Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
title Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
title_full Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
title_fullStr Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
title_full_unstemmed Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
title_short Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
title_sort diastereoselective synthesis of 3,4-dihydro-2h-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082461/
https://www.ncbi.nlm.nih.gov/pubmed/27829915
http://dx.doi.org/10.3762/bjoc.12.198
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