Acylimines of hexafluoroacetone in cyclocondensation with C,N-binucleophiles

Abstract

The reactions of acylimines of hexafluoroacetone with 1,3 C,N binucleophiles giving rise to fluorine containing 1,4 dihydropyrimidines, including fused compounds, were studied.

Synthesis of bis(trifluoromethyl)pyrimido[4,5-d]pyrimidine-2,4-diones and evaluation of their antibacterial and antifungal activities

“…In our previous works, a new approach to the construction of trifluoromethylated pyrimido [4,5-d]pyrimidine ring systems by the cyclocondensation of N-acylimines of hexafluoroacetone or methyl trifluoropyruvate with 6-aminouracils/thiouracils was reported [19][20][21][22]. Thus, in continuation of our research in the field of bioactive heterocyclic compounds, a number of unexplored fluorinated pyrimido [4,5-d]pyrimidines were synthesized and their antibacterial and antifungal activities were evaluated.…”

Esters of 2-aryl-2-isocyanato-3,3,3-trifluoropropionic acid in cyclocondensation with amines

“…The derivatives of esters of trifluoropyruvic acid, like N-substituted imines of trifluoropyruvates, are successfully used in the synthesis of fluorinated heterocyclic compounds [1][2][3][4][5]. The most promising in this respect is the use of these reagents as 1,3-bielectrophiles in the reactions of cyclocondensation [6][7][8][9][10]. The goal of the present study is the synthesis of new bielectrophiles based on ethyl fluoropyruvate, that is, the esters of 2-aryl-2-isocyanato-3,3,3-trifluoropropionic acid, and investigation of their behavior in the reactions of cyclocondensation.…”

Modification of biologically active amides and amines with fluorine-containing heterocycles 4. Trifluoromethyl-containing heterocyclic pyracetam derivatives

“…The pre sent work was prompted by the data obtained during the study of behavior of hexafluoroacetone N acylimines (2) in the cyclocondensation reactions with 1,3 N,N and 1,3 C,N binucleophiles, which lead to the forma tion of six membered trifluoromethyl containing hetero cycles. 3- 5 We failed to obtain the starting bielectrophilic reagent, hexafluoroacetone 2 (2 oxopyrrolidin 1 yl)acetylimine (3), in the individual state using known 3 methods for the synthesis of hexafluoroacetone N substituted imines. Therefore, imine 3 was generated in situ by sequential addition of pyridine, hexafluoroacetone 2, and thionyl chloride to a solution of compound 1 in DMF with subse quent involvement of imine 3, without isolation in the individual state, into the cyclocondensation with 1,3 C,N and N,N binucleophiles (Scheme 1).…”