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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Main Authors:	Mikhail Yu. Ievlev, Oleg V. Ershov, Mikhail Yu. Belikov, Angelina G. Milovidova, Viktor A. Tafeenko, Oleg E. Nasakin
Format:	Article
Language:	English
Published:	Beilstein-Institut 2016-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	diastereoselectivity 3,4-dihydro-2H-pyran-4-carboxamide nitriles pyran quasi-hydrolysis
Online Access:	https://doi.org/10.3762/bjoc.12.198

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spelling	doaj-fc6583f99e134fdb858be74cce1cbd0a2021-02-02T04:31:08ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-09-011212093209810.3762/bjoc.12.1981860-5397-12-198Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano groupMikhail Yu. Ievlev0Oleg V. Ershov1Mikhail Yu. Belikov2Angelina G. Milovidova3Viktor A. Tafeenko4Oleg E. Nasakin5Department of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, RussiaDepartment of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, RussiaDepartment of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, RussiaDepartment of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, RussiaDepartment of General Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, RussiaDepartment of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, RussiaAn 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.https://doi.org/10.3762/bjoc.12.198diastereoselectivity3,4-dihydro-2H-pyran-4-carboxamidenitrilespyranquasi-hydrolysis
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Mikhail Yu. Ievlev Oleg V. Ershov Mikhail Yu. Belikov Angelina G. Milovidova Viktor A. Tafeenko Oleg E. Nasakin
spellingShingle	Mikhail Yu. Ievlev Oleg V. Ershov Mikhail Yu. Belikov Angelina G. Milovidova Viktor A. Tafeenko Oleg E. Nasakin Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group Beilstein Journal of Organic Chemistry diastereoselectivity 3,4-dihydro-2H-pyran-4-carboxamide nitriles pyran quasi-hydrolysis
author_facet	Mikhail Yu. Ievlev Oleg V. Ershov Mikhail Yu. Belikov Angelina G. Milovidova Viktor A. Tafeenko Oleg E. Nasakin
author_sort	Mikhail Yu. Ievlev
title	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_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_sort	diastereoselective synthesis of 3,4-dihydro-2h-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2016-09-01
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.
topic	diastereoselectivity 3,4-dihydro-2H-pyran-4-carboxamide nitriles pyran quasi-hydrolysis
url	https://doi.org/10.3762/bjoc.12.198
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Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

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