975-16-6Relevant academic research and scientific papers
Synthesis and structures of stable phosphorus zwitterions derived from mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates
Saijo, Ryosuke,Uno, Hidemitsu,Mori, Shigeki,Kawase, Masami
supporting information, p. 8006 - 8009 (2016/07/06)
Trialkyl phosphites were evaluated as phosphorus nucleophiles for addition to mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), thereby producing tetravalent phosphorus zwitterions (2) in good yields. The structure of 2 was determined to be a tetrav
Facile synthesis of imidazo[1,5-a]pyrazin-8(7H)-ones from mesoionic 1,3-oxazolium-5-olates via a multistep one-pot transformation
Saijo, Ryosuke,Uno, Hidemitsu,Kawase, Masami
, p. 2047 - 2058 (2016/11/25)
A novel one-pot conversion of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates into imidazo[1,5-a]pyrazin-8(7H)-ones by the reaction with TosMIC is described. The structure of the product was determined by single-crystal X-ray analysis.
Synthesis and Cycloaddition Reactions of Stabilized Münchnones
Kakaawla, Taban K. K.,Hartley, Will C.,Harrity, Joseph P. A.
supporting information, p. 2789 - 2792 (2016/07/07)
A family of stabilized münchnones bearing an acyl group at C4 have been prepared and studied in alkyne cycloaddition reactions. These reactions are highly regioselective, and the method represents a rapid and straightforward route to densely substituted pyrroles. Finally, the C4-stabilizing units can be further manipulated to furnish carboxylic acid and amide groups, or removed altogether to provide unsubstituted pyrroles.
Cyclocondensation reaction of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5- olates with hydroxylamine affording 6-trifluoromethyl-5,6-dihydro-4h-1,2,4- oxadiazin-6-ols
Saijo, Ryosuke,Kurihara, Ken-Ichi,Akira, Kazuki,Kawase, Masami
, p. 115 - 123 (2013/03/13)
Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) undergo tandem addition of hydroxylamine to afford 6-trifluoromethyl-1,2,4-oxadiazin-6-ols (3) in high yields.
New synthesis of 3-trifluoromethylpyrroles by condensation of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates with phosphorus ylides
Saijo, Ryosuke,Hagimoto, Yuri,Kawase, Masami
supporting information; experimental part, p. 4776 - 4779 (2011/01/03)
Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give β-trifluoromethylpyrroles (2) in good yields. The novel ring transformations
Convenient synthesis of 4-trifluoromethyl-substituted imidazole derivatives
Kawase,Saito,Kurihara
, p. 461 - 464 (2007/10/03)
Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines (2) with trifluoroacetic anhydride, react with ammonia to give 4-trifluoromethyl-3,4-dihydroimidazoles (3) in high yields. Dehydration of 3 gives
Convenient synthesis of 5-trifluoroacetylated imidazoles by ring transformation of mesoionic 1,3-oxazolium-5-olates
Kawase, Masami,Saito, Setsuo
, p. 410 - 414 (2007/10/03)
Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines (2) with trifluoroacetic anhydride, react with amidines to give 5-trifluoroacetylimidazoles (3) in moderate yield. The novel ring transformations of 1 into 3 occur via an initial attack of amidines on the C-2 position of the ring.
AN EFFICIENT SYNTHESIS OF 4-TRIFLUOROMETHYLATED AND 4-PERFLUOROALKYLATED IMIDAZOLES FROM MESOIONIC 1,3-OXAZOLIUM-5-OLATES
Kawase, Masami,Saito, Setsuo,Kurihara, Teruo
, p. 1617 - 1620 (2007/10/03)
4-Trifluoromethyl- and 4-perfluoroalkylimidazoles (4) were conveniently synthesized from mesoionic 4-trifluoroacetyl- or 4-perfluoroacyl-1,3-oxazolium-5-olate (1) via 2-imidazolines (3), which were formed through the regioselective attack of ammonia on the C(2) position of 1.
