Abstract
A facile method of trifluoroacylation of imidazoles, 1,3-thiazoles, and 1,3-oxazoles
with trifluoroacetic anhydride resulted in a set of heterocyclic trifluoromethyl-containing
ketones. Unlike common ketones, these compounds form stable hydrates and enter into
noncatalytic ene reactions with terminal olefins affording the corresponding allyl
alcohols.
Key words
fluorine compounds - acylations - ketones - nitrogen-containing heterocycles - stable
hydrates
References
<A NAME="RP13307SS-1A">1a </A>
Filler R.
Kobayashi Y.
Yagupolskii LM.
Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications
Elsevier;
Amsterdam:
1993.
<A NAME="RP13307SS-1B">1b </A> Kukhar V. P., Soloshonok V. A.; Fluorine-Containing Amino Acids, Synthesis and
Properties; Wiley: New York, 1995 ;
<A NAME="RP13307SS-1C">1c </A>
Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639
Ojima I.
McCarthy JR.
Welch JT.
American Chemical Society;
Washington D.C.:
1996.
<A NAME="RP13307SS-2A">2a </A>
Lin P.
Jiang J.
Tetrahedron
2000,
56:
3635 ; and references cited therein
<A NAME="RP13307SS-2B">2b </A>
Dolenský B.
Kvíčala J.
Paleček J.
Paleta O.
J. Fluorine Chem.
2002,
115:
67
<A NAME="RP13307SS-2C">2c </A>
Friezer RW.
Ducharme Y.
Ball RG.
Blouin M.
Boulet L.
Côté B.
Frenette R.
Girard M.
Guay D.
Huang Z.
Jones TR.
Laliberté F.
Lynch JJ.
Mancini J.
Martins E.
Masson P.
Muise E.
Pon DJ.
Siegl PKS.
Styhler A.
Tsou NN.
Turner MJ.
Young RN.
Girard Y.
J. Med. Chem.
2003,
46:
2413
<A NAME="RP13307SS-3A">3a </A> For hexafluoroacetone hydrate, see:
Middleton L.
J. Am. Chem. Soc.
1964,
86:
4948
<A NAME="RP13307SS-3B">3b </A> For methyl trifluoro-pyruvate hydrate, see:
Palecek J.
Paleta O.
Synthesis
2004,
521
<A NAME="RP13307SS-4A">4a </A>
Braun RA.
J. Org. Chem.
1966,
31:
3828
<A NAME="RP13307SS-4B">4b </A>
Saloutin VI.
Piterskikh IA.
Pashkevich KI.
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)
1986,
35:
570
<A NAME="RP13307SS-5">5 </A>
Ohkura H.
Berbasov DO.
Soloshonok VA.
Tetrahedron
2003,
59:
1647
<A NAME="RP13307SS-6A">6a </A>
Chkanikov ND.
Sviridov VD.
Zelenin AE.
Galakhov MV.
Kolomiets AF.
Fokin AV.
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)
1990,
39:
323
<A NAME="RP13307SS-6B">6b </A>
Masciardi R.
Kamer M.
Nock N.
Eur. J. Org. Chem.
2003,
4286
<A NAME="RP13307SS-7A">7a </A>
Soloshonok VA.
Khotkevich AB.
Krasutskii PA.
J. Org. Chem. USSR (Engl. Transl.)
1991,
27:
641
<A NAME="RP13307SS-7B">7b </A>
Kobayashi Y.
Nagai T.
Kumadaki I.
Chem. Pharm. Bull.
1984,
32:
5031
<A NAME="RP13307SS-7C">7c </A>
Iseki K.
Nagai T.
Kobayashi Y.
Chem. Pharm. Bull.
1992,
32:
1346
<A NAME="RP13307SS-7D">7d </A>
Urry WH.
Niu JHY.
Lundsted LG.
J. Org. Chem.
1968,
33:
2302
<A NAME="RP13307SS-8A">8a </A>
Golubev AS.
Kolomiets AF.
Fokin AV.
J. Fluorine Chem.
1991,
54:
273
<A NAME="RP13307SS-8B">8b </A>
Golubev AS.
Galakhov MV.
Kolomiets AF.
Fokin AV.
Bull. Russ. Acad. Sci., Div. Chem. Sci. (Engl. Transl.)
1992,
41:
2193
<A NAME="RP13307SS-9">9 </A>
Lermontov SA.
Shkavrov SV.
Kuryleva NV.
J. Fluorine Chem.
2003,
121:
223
<A NAME="RP13307SS-10A">10a </A>
Regel E.
Büchel KH.
Justus Liebigs Ann. Chem.
1977,
145
<A NAME="RP13307SS-10B">10b </A>
Kawase M.
Sakagami H.
Kusama K.
Motohashi N.
Saito S.
Bioorg. Med. Chem. Lett.
1999,
9:
3113
<A NAME="RP13307SS-10C">10c </A>
Fujii S.
Maki Y.
Kimoto H.
J. Fluorine Chem.
1987,
35:
437
<A NAME="RP13307SS-10D">10d </A>
Salvador RL.
Saucier M.
Tetrahedron
1971,
27:
1221
<A NAME="RP13307SS-11A">11a </A>
Tolmachev AA.
Yurchenko AA.
Merculov AS.
Semenova MG.
Zarudnitskii EV.
Ivanov VV.
Pinchuk AM.
Heteroat. Chem.
1999,
10:
585
<A NAME="RP13307SS-11B">11b </A>
Komarov IV.
Strizhak AV.
Kornilov MY.
Zarudnitskiy EV.
Tolmachev AA.
Synth. Commun.
2000,
30:
243
<A NAME="RP13307SS-11C">11c </A>
Zarudnitskii EV.
Ivanov VV.
Yurchenko AA.
Pinchuk AM.
Tolmachev AA.
Heteroat. Chem.
2002,
13:
146
<A NAME="RP13307SS-11D">11d </A>
Ivanov VV.
Yurchenko AA.
Chernega AN.
Pinchuk AM.
Tolmachev AA.
Heteroat. Chem.
2002,
13:
84
<A NAME="RP13307SS-11E">11e </A>
Zarudnitskii EV.
Pervak II.
Merkulov AS.
Yurchenko AA.
Tolmachev AA.
Pinchuk AM.
Synthesis
2006,
1279
<A NAME="RP13307SS-12A">12a </A>
Hlasta D.
Tetrahedron Lett.
1990,
31:
5833
<A NAME="RP13307SS-12B">12b </A>
Humburg G.
Mildenberger H.
Liebigs Ann. Chem.
1982,
1387
<A NAME="RP13307SS-12C">12c </A>
Alemagna A.
Bacchetti T.
Gazz. Chim. Ital.
1972,
102:
1068
<A NAME="RP13307SS-13">13 </A>
Begtrup M.
Larsen P.
Acta Chem. Scand.
1990,
44:
1050
<A NAME="RP13307SS-14">14 </A>
LaMattina JL.
J. Org. Chem.
1980,
45:
2261
<A NAME="RP13307SS-15">15 </A>
Ainsworth C.
J. Am. Chem. Soc.
1958,
80:
5201
<A NAME="RP13307SS-16">16 </A>
Bower JD.
Ramage GR.
J. Chem. Soc.
1955,
2834
<A NAME="RP13307SS-17">17 </A>
Ainsworth C.
J. Am. Chem. Soc.
1955,
77:
1148
<A NAME="RP13307SS-18">18 </A>
Sheldrick, G. M., SHELXTL PLUS. PC Version. A system of computer programs for the
determination of crystal structure from X-ray diffraction data. Rev. 5.1, 1998.