Abstract
Heterocyclization of 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-tienyl]-3-buten-2-one and 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-furyl]-3-buten-2-ones into isoxazoles and pyrazoles derivatives as a new type of trihalomethylated bicyclic heterocycles is reported.
Keywords
[3+2] cyclocondensation - furyl isoxazoles - thienyl isoxazoles - furyl pyrazoles - thienyl pyrazoles
References
1 For part 18 in this series, see: Martins MAP.
Bastos GP.
Sinhorin AP.
Zimmermann NEK.
Rosa A.
Brondani S.
Emmerich D.
Bonacorso HG.
Zanatta N.
J. Fluorine Chem.
2003,
123:
249
2a
Frolund B.
Jorgensen AT.
Tagmose L.
Stensbol TB.
Vertergaard HT.
Engblom C.
Kristiansen U.
Sanchez C.
Krogsgaard-Laesen P.
Liljefors T.
J. Med. Chem.
2002,
45:
2454
2b
Frolund B.
Tagmose L.
Liljefors T.
Stensbol TB.
Engblom C.
Kristiansen U.
Krogsgaard-Larsen P.
J. Med. Chem.
2000,
43:
4930
2c
Habeeb AG.
Praveen Rao PN.
Knaus EE.
J. Med. Chem.
2001,
44:
3039
2d
Clark RD.
J. Agric. Food Chem.
1996,
44:
3643
2e
Donohue BA.
Michelotti EL.
Reader JC.
Reader V.
Stirling M.
Tice CM.
J. Comb. Chem.
2002,
4:
23
3a
Grünanger P.
Vita-Finzi P. In
Chemistry of Heterocyclic Compounds: Isoxazoles
Vol. 49, Part 1:
Wiley;
New York:
1991.
3b
Singh SP.
Kumar D.
Batra H.
Naithani R.
Rozas I.
Elguero J.
Can. J. Chem.
2000,
78:
1109
3c
Elguero J. In
Comprehensive Heterocyclic Chemistry
Vol. 5, 1st ed.:
Katrittzky AR.
Rees CW.
Pergamon/Elsevier;
Oxford:
1984.
p.167
4a
Baurle P. In Electronic Materials: The Oligomeric Approach
Müllen K.
Wegner G.
Wiley-VCH;
Weinheim:
1998.
Chap. 2.
4b
Otsubo T.
Aso Y.
Takimiya K.
Bull. Chem. Soc. Jpn.
2001,
74:
1789
4c
Fichou D.
J. Mater. Chem.
2000,
10:
571
4d
Dodabalapur A.
Torsi H.
Katz HE.
Science
1995,
268:
270
5a
Martins MAP.
Bastos GP.
Bonacorso HG.
Zanatta N.
Flores AFC.
Siqueira GM.
Tetrahedron Lett.
1999,
40:
4309
5b
Bonacorso HG.
Martins MAP.
Bittencourt SRT.
Lourega RV.
Zanatta N.
Flores AFC.
J. Fluorine Chem.
1999,
99:
177
6a In Organofluorine Chemistry: Principles and Commercial Applications
Banks RE.
Smart BE.
Tatlow JC.
Plenum;
New York:
1994.
6b In Organic Chemistry in Medicinal Chemistry and Biochemical Applications
Filler R.
Elsevier;
Amsterdam:
1993.
6c
Sargent CR.
Adv. Heterocyclic Chem.
1991,
28:
1
6d
Clark RD.
J. Agric. Food Chem.
1996,
44:
3643
6e
Habeeb AG.
Praveen Rao PN.
Knaus EE.
J. Med. Chem.
2001,
44:
3039
7a
Jiang B.
Xu Y.-Y.
Yang J.
J. Fluorine Chem.
1994,
67:
83
7b
Plancquaert M.-A.
Redon M.
Janousek Z.
Viehe HG.
Tetrahedron
1996,
52:
4383
7c
Bravo P.
Diliddo D.
Resnati G.
Tetrahedron
1994,
50:
8827
7d
Touzot A.
Soufyane M.
Berber H.
Toupet L.
Mirand C.
J. Fluorine Chem.
2004,
125:
1299
7e
Sloop JC.
Bumgardner CL.
Loehle WD.
J. Fluorine Chem.
2002,
118:
135
7f
Sevenard DV.
Khomutov OG.
Pashkevich KI.
Lork E.
Röschenthaler G.-V.
Helv. Chim. Acta
2002,
85:
1960
8a
Martins MAP.
Cunico W.
Pereira CMP.
Sinhorin A.
Flores AFC.
Bonacorso HG.
Zanatta N.
Curr. Org. Chem.
2004,
1:
391
8b
Martins MAP.
Pereira CMP.
Zimmermann NEK.
Moura S.
Sinhorin A.
Cunico W.
Zanatta N.
Bonacorso HG.
Flores AFC.
Synthesis
2003,
2353
9
Flores AFC.
Brondani S.
Zanatta N.
Rosa A.
Martins MAP.
Tetrahedron Lett.
2002,
43:
8701
10
19 F NMR in CDCl3 from external CFCl3 (δ = 0.0 ppm): for 5-trifluoromethyl-4,5-dihydroisoxazoles and 5-trifluoromethyl-1-phenyl-4,5-dihydropyrazoles the δ were in range -78.1 to -82.9 ppm; for 5-trifluoromethylisoxazoles δ = -64.1 to -64.5 ppm; for 5-trifluoromethyl-1H -pyrazoles δ = -62.8 to -63.5 ppm; from a mixture of isomers ( [1,3] 15a′ and [1,5] 15a ) were obtained two signals at -62.8 and -64.1 ppm with the same intensity.
11a
Claramunt RM.
Lopez C.
Trofimenko S.
Elguero J.
Can. J. Chem.
1993,
71:
678
11b
Foces-Foces C.
Trofimenko S.
Lopez C.
Santa Maria MD.
Claramunt RM.
Elguero J.
J. Mol. Struct.
2000,
526:
59
12
Martins MAP.
Flores AFC.
Bastos GP.
Sinhorin AP.
Zanatta N.
Bonacorso HG.
Tetrahedron Lett.
2000,
41:
293
13
Chapman AV.
Cook MJ.
Katritzky AR.
Aabraham MH.
Danil de Namor AF.
Dumont L.
Reisse J.
Tetrahedron
1978,
34:
1571