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

ABSTRACT: 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.

SUBMITTER: Ievlev MY

PROVIDER: S-EPMC5082461 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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

Ievlev Mikhail Yu MY Ershov Oleg V OV Belikov Mikhail Yu MY Milovidova Angelina G AG Tafeenko Viktor A VA Nasakin Oleg E OE

Beilstein journal of organic chemistry 20160927

An efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2<i>H</i>-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. ...[more]

PMID: 27829915

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