Reaction of trifluoromethyl 1,3-dicarbonyl compounds with formaldehyde and esters of natural α-aminoacids

Reaction of trifluoromethyl 1,3-dicarbonyl compounds with formaldehyde and esters of natural α-aminoacids Full article

Journal

Arkivoc
ISSN: 1551-7012 , E-ISSN: 1551-7004

Output data

Year: 2017, Number: 4, Pages: 222-235 Pages count : 14 DOI: 10.24820/ark.5550190.p010.003

Authors

Gibadullina Natalya N. ¹ , Latypova Dilara R. ^1,2 , Novikov Roman A. ^3,2 , Tomilov Yury V. ^3,2 , Dokichev Vladimir A. ^1,2

Affiliations

1	Ufa Institute of Chemistry of the Russian Academy of Sciences, 71 prospect Oktyabrya, Ufa, 450 054, Russian Federation
2	Ufa State Aviation Technical University, 12 K. Marx Street, Ufa, 450 008, Russian Federation
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119 991 Moscow, Russian Federation

Condensation of fluorinated 1,3-dicarbonyl compounds with formaldehyde and l-amino acid ester hydrochlorides in acetate buffer, AcONa–AcOH (pH 5.9), at room temperature gave chiral hexahydropyrimidines, both containing and lacking a trifluoroacetyl group at position 5 of the heterocycle. In contrast, the reaction of ethyl 3-oxo-4,4,4-trifluorobutanoate with formaldehyde and ethyl (S)-tyrosinate hydrochloride under the same conditions gave a new chiral tetrahydropyrimidinium salt containing the trifluoroacetate anion in good yield. It is interesting that one of the formaldehyde molecules acts as an oxidant in this process.

Gibadullina N.N. , Latypova D.R. , Novikov R.A. , Tomilov Y.V. , Dokichev V.A.
Reaction of trifluoromethyl 1,3-dicarbonyl compounds with formaldehyde and esters of natural α-aminoacids
Arkivoc. 2017. N4. P.222-235. DOI: 10.24820/ark.5550190.p010.003 Scopus OpenAlex

≡ Scopus:	2-s2.0-85036524455
≡ OpenAlex:	W2772593038