H.G. Bonacorso et al. / Journal of Fluorine Chemistry 132 (2011) 160–165
165
13C NMR (DMSO-d6):
d
= 194.6 (C55O, Bz), 194.4 (C5), 165.9
303.296/2008–9) and the 13C NMR analyses from Chemistry
Department of Santa Catarina Federal University (UFSC/Brazil).
Fellowships from CAPES and CNPq are also acknowledged.
1
(C8a), 164.4 (d, JCF = 253 Hz, Ar), 140.9, 133.9 (Ar), 130.1 (d,
3JCF = 9 Hz, Ar), 127.6, 127.2, 125.8 (Ar), 121.6 (q, JCF = 287 Hz,
1
2
2
CF3), 115.1 (d, JCF = 22 Hz, Ar), 114.8 (C4a), 94.6 (q, JCF = 33 Hz,
C2), 49.0 (C3), 38.7 (C6), 36.3 (C8), 27.7 (C4), 19.3 (C7).
Appendix A. Supplementary data
19F NMR (DMSO-d6):
d
= À80.37 (CF3), À105.0 (4-FPh). MS (ESI)
m/z: [(M+H)+, 435.1], [(M+Na)+, 457.2]. IR (KBr)
max: 3453, 1688,
1603, 1358, 1241, 1188, 1160, 845 cmÀ1
Anal. Calcd. for
23H18F4O4 (434.11): C, 63.60; H, 4.18%. Found: C, 63.70; H, 4.46%.
n
Supplementary data associated with this article can be found, in
.
C
4.2.1.4. 3-(Furan-2-oyl)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-
References
3,4,7,8-tetrahydro-2H-chromen-5(6H)-one (4ad). Yellow solid, yield
47%, mp 190–191 8C. 1H NMR (DMSO-d6):
d = 8.55 (s, 1H, OH),
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13C NMR (DMSO-d6):
d = 195.0 (C5); 182.9 (C55O, Fur), 166.3
(C8a), 152.3 (Fur), 148.6 (Fur), 141.2, 127.8, 127.6, 126.0 (Ph), 121.8
(q, 1JCF = 287 Hz, CF3), 119.5 (Fur), 115.0 (C4a), 112.6 (Fur), 94.8 (q,
2JCF = 33 Hz, C2), 49.5 (C3), 38.2 (C6), 36.5 (C8), 27.9 (C4), 19.6 (C7).
19F NMR (DMSO-d6):
d
= À80.67 (CF3). MS (ESI) m/z: [(M+H)+,
407.1], [(M+Na)+, 429.1]. IR (KBr)
nmax: 3447, 1673, 1608, 1426,
1358, 1189, 1163, 1040, 764, 732 cmÀ1. Anal. Calcd. for C21H17F3O5
(406.10): C, 62.07; H, 4.22%. Found: C, 61.94; H, 4.51%.
4.2.1.5. 2-Hydroxy-4-phenyl-3-(thien-2-oyl)-2-(trifluoromethyl)-
3,4,7,8-tetrahydro-2H-chromen-5(6H)-one (4ae). White solid, yield
50%, mp 187–189 8C; (Lit. [3]: 222–223 8C). 1H NMR (DMSO-d6):
(b) L.L. Andreani, E. Lapi, Bull. Chim. Farm. 99 (1960) 583;
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96 (1982) 135383e;
(d) E.C. Witte, P. Neubert, A. Roesch, D.E. Ger. Offen., Chem. Abstr. 104 (1986)
224915f;
d
= 8.55 (s, 1H, OH), 7.80 (d, J = 5 Hz, 1H, Th), 7.41 (s, 1H, Th), 7.07–
7.04 (m, 4H, Ar), 6.97–6.96 (m, 2H, Ph/Th), 4.19 (d, J = 12 Hz, 1H,
H3), 3.98 (d, J = 12 Hz, 1H, H4), 2.62–2.57 (m, 2H, H6), 2.20–2.18
(m, 2H, H8), 1.97–1.95 (m, 2H, H7).
(e) L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28 (1993) 517.
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13C NMR (DMSO-d6):
d = 194.6 (C5), 188.1 (C55O, Th), 166.0
(C4a), 144.5 (Th), 140.9 (Ph), 135.7 (Th), 132.9 (Th), 128.2 (Ph),
127.6 (Th), 127.3, 125.8 (Ph), 121.7 (q, JCF = 287 Hz, CF3), 114.9
(C4a), 94.6 (q, 2JCF = 33 Hz, C2), 50.9 (C3), 38.6 (C6), 36.3 (C8), 27.8
1
(C4), 19.4 (C7).
19F NMR (DMSO-d6):
d
= À81.41 (CF3). MS (ESI) m/z: [(M+H)+,
423.0], [(M+Na)+, 445.0]. IR (KBr)
nmax: 3420, 1659, 1609, 1361,
1259, 1189, 1163, 1020, 729, 709 cmÀ1
21H17F3O4S (422.08): C, 59.71; H, 4.06%. Found: C, 59.81; H, 4.32%.
. Anal. Calcd. for
(d) M. Hojo, R. Masuda, E. Okada, Tetrahedron Lett. (1986) 1013;
(e) F. Effenberger, R. Maier, K.H. Schonwalder, T. Ziegler, Chem. Ber. 115 (1982)
2766;
C
(f) M. Hojo, R. Masuda, E. Okada, Synthesis (1986) 1013;
(g) M. Hojo, R. Masuda, S. Sakaguchi, M. Takagawa, Synthesis (1986) 1016;
(h) A. Colla, M.A.P. Martins, G. Clar, S. Krimmer, P. Fischer, Synthesis (1991) 483;
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(1994) 24;
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4.2.1.6. 2-Hydroxy-3-(naphth-1-oyl)-4-phenyl-2-(trifluoromethyl)-
3,4,7,8-tetrahydro-2H-chromen-5(6H)-one (4af). White solid, yield
12%, mp 199–200 8C. 1H NMR (DMSO-d6):
d = 8.70 (s, 1H, OH), 8.37
(d, J = 8.0 Hz, 1H, Ar), 7.97 (d, J = 8 Hz, 1H, Ar) 7.90 (d, J = 8 Hz, 1H,
Ar), 7.60–7.51 (m, 2H, Ar), 7.24–7.11 (m, 5H, Ar), 7.07–7.05 (m, 1H,
Ar), 6.88 (d, J = 7 Hz, 1H, Ar), 4.37 (d, J = 12 Hz, 1H, H3), 4.17 (d,
J = 12 Hz, 1H, H4), 2.64–2. 53 (m, 2H, H6), 2.25–2.22 (m, 2H, H8),
2.00–1.97 (m, 2H, H7).
(l) H.G. Bonacorso, C.A. Cechinel, M.R. Oliveira, M.B. Costa, M.A.P. Martins, N.
Zanatta, A.F.C. Flores, J. Heterocycl. Chem. 42 (2005) 1055.
[16] Crystallographic data for the structure of 4aa, reported in this paper have been
deposited with the Cambridge Crystallographic Data Centre and allocated the
deposition number CCDC 774510. Copies of the data can be obtained free of
charge, on application to CCDC 12 Union Road, Cambridge CB2 1EZ, UK. (fax: +44
[17] Bruker, APEX2 (Version 2.1), COSMO (Version 1.56), BIS (Version 2.0.1.9), SAINT
(Version 7.3A) and SADABS (Version 2004/1) and XPREP9 (Version 2005/4),
Bruker AXS Inc., Madison, WI, USA, 2006.
13C NMR (DMSO-d6):
d = 197.0 (C55O, Naph.), 194.7 (C5), 166.0
(C8a), 141.6, 135.3, 133.0, 132.8, 129.2, 128.0, 127.9, 127.5, 127.3,
127.2, 126.2, 125.9, 125.1, 123.8 (Ar), 120.7 (q, 1JCF = 287 Hz, CF3),
114.8 (C4a), 94.6 (q, 2JCF = 33 Hz, C2), 52.7 (C3), 38.2 (C6), 36.3 (C8),
27.7 (C4), 19.4 (C7).
19F NMR (DMSO-d6):
d
= À77.0 (CF3). MS (ESI) m/z (%): [(M+H)+,
467.1], [(M+Na)+, 489.1]. IR (KBr)
nmax: 3428, 1678, 1607, 1349,
[18] G.M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, University of
Go¨ttingen, Germany, 1997.
[19] G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University
of Go¨ttingen, Germany, 1997.
1230, 1193, 1039, 1016, 736, 654 cmÀ1. Anal. Calcd. for C27H21F3O4
(466.14): C, 69.52; H, 4.54%. Found: C, 69.09; H, 5.01%.
[20] P. Coppens, L. Leiserowitz, D. Rabinovich, Acta Crystallogr. 18 (1965) 1035.
[21] L.J. Farrugia, J. Appl. Crystallogr. 30 (1997) 565.
[22] P. Pyykko, Chem. Rev. 97 (1997) 597.
Acknowledgements
[23] (a) M. Hojo, R. Masuda, E. Okada, Synthesis (1990) 347;
(b) S. Zhu, G. Jin, W. Peng, Q. Huang, Tetrahedron 59 (2003) 2899;
(c) I.I. Gerus, L.M. Kacharova, S.I. Vdovenko, Synthesis (2001) 431.
The authors thank the financial support from Conselho Nacional
´
´
de Desenvolvimento Cientıfico e Tecnologico – CNPq (Proc.