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 process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation.
Department of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, Russia.
Mikhail Yu
MY
Ievlev
Department of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, Russia.
Oleg V
OV
Ershov
Department of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, Russia.
Mikhail Yu
MY
Belikov
Department of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, Russia.
Angelina G
AG
Milovidova
Department of General Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, Russia.
Viktor A
VA
Tafeenko
Department of Organic and Pharmaceutical Chemistry, Ulyanov Chuvash State University, Moskovskiy av. 15, Cheboksary, Russia.
Oleg E
OE
Nasakin
3,4-dihydro-2H-pyran-4-carboxamide; diastereoselectivity; nitriles; pyran; quasi-hydrolysis