Synthesis of fluorinated 2‐oxo‐1,4,2‐oxazaphosphol‐4‐ines and their opening by alcohols

Abstract

Trifluoromethyl-substituted I ,4,2A5-oxazaphosphol-4-ines from phosphorus dichlorides and N-acylimines

Fluorinated α-aminoalkylphosphoryl Compounds. Synthesis, Chemical Properties and Biological Activitiy

“…Так, в результате реакции [1+4]-циклоприсоединения иминов гексафторацетона 1 с дихлорфосфитами в среде SO 2 образуются 1,4,2-оксазафосфолы 3, которые в дальнейшем мягко раскрываются различными нуклеофилами по внутримолекулярной Р-О-связи с образованием соответствующих a-аминофосфонатов и a-аминофосфинатов 4 [3][4][5] (схема 1).…”

Reactions of methyl trifluoropyruvate 2-pyridylimines with trimethyl phosphite

“…In this work, we studied the reactions of methyl trifluoropyruvate 2 pyridylimines 1 with trimethyl phos phite (2). This study was preceded by the known data on the reactions of hexafluoroacetone and methyl trifluoro pyruvate N acylimines with trimethyl phosphite.…”

Acylimines of hexafluoroacetone in cyclocondensation with C,N-binucleophiles

“…Acylimines of hexafluoroacetone serve as synthons for the synthesis of various heterocyclic compounds contain ing geminal trifluoromethyl groups and are used as heterodienes and dienophiles in cycloaddition with ni triles, 1,2 derivatives of trivalent phosphorus acids, 3 and cyclopentadiene 4 as well as 1,3 bielectrophilic reagents in cyclocondensation with 1,3 binucleophiles 5, 6 to give oxadiazines, oxazaphospholenes, azanorbornenes, and dihydrotriazines, respectively. In the present study, we examined the synthetic possibilities of acylimines of hexafluoroacetone 1 as 1,3 bielectrophilic reagents for the preparation of 1,4 dihydropyrimidines by cyclo condensation with 1,3 C,N binucleophiles.…”

“…Cyclocondensation of imines 1a-k with 2 amino crotononitrile 2, 6 aminouracils 5a-d, 6 aminothio uracils 6a,b, and N substituted 3 aminocyclohexenones 7a-c (equimolar amounts of the reagents were mixed in DMF at 20 °C and, after completion of the exother mic reaction, the mixture was heated in the presence of catalytic amounts of Et 3 Therefore, acylimines of hexafluoroacetone can be successfully used as 1,3 bielectrophiles in the synthesis of various previously unknown 4,4 bis(trifluoromethyl) 1,4 dihydropyrimidines, including fused derivatives. The ease of the preparation of the latter is determined primarily by the ease of the preparation of 1,3 C,N binucleophiles, the available procedures for the synthesis of acylimines of hexafluoroacetone, 1,10 and the experimental simplicity of the developed method.…”