G
Synthesis
J. A. Cabezas, N. Ferllini
Paper
1
H NMR (CDCl , 400 MHz): = 7.17 (dd, J = 5.2, 1.1 Hz, 1 H), 7.11 (br d,
(11) Negishi, E. I.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957.
3
J = 3.6 Hz, 1 H), 6.93 (dd, J = 5.2, 3.6 Hz, 1 H), 2.08 (s, 3 H).
(12) For a historical review on palladium-catalyzed cross-coupling
reactions, see: Johansson-Seechurn, C. C. C.; Kitching, M. O.;
Colacot, T. J.; Snieckus, V. Angew. Chem. Int. Ed. 2012, 51, 5062.
13
C NMR (CDCl , 100 MHz): = 130.7, 126.5, 125.6, 124.0, 89.8, 72.7,
3
4.4.
(13) Negishi, E. I.; Akiyoshi, K.; Takahashi, T. J. Chem. Soc., Chem.
Commun. 1987, 477.
MS (EI): m/z (%) = 39 (8), 51 (13), 63 (15), 77 (21), 96 (28), 121 (97),
+
1
22 (100) [M] .
(14) For a review on the synthesis of heterocyclic compounds
through substituted alkynes, see: Pal, M. Synlett 2009, 2896.
+
+
HRMS (ESI, V ): m/z [M + H] calcd for C H S: 123.0268; found:
7
7
123.0267.
(15) Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun. 1993, 86.
16) Chen, L.; Li, Y.; Xu, M. H. Org. Biomol. Chem. 2010, 8, 3073.
(
2
-Phenyl-5-(propyn-1-yl)thiophene (3)
(17) (a) Kundu, N. G.; Pal, M.; Mahanty, J. S.; Dasgupta, S. K. J. Chem.
Soc., Chem. Commun. 1992, 41. (b) Kundu, N. G.; Pal, M.;
Mahanty, J. S.; De, M. J. Chem. Soc., Perkin Trans. 1 1997, 2815.
[
CAS Reg. No. 1204-82-6]
Yield: 0.126 g (97%); yellow solid.
(c) Arcadi, A.; Blesi, F.; Cacchi, S.; Fabrizi, G.; Goggiamani, A. Tet-
1
H NMR (CDCl , 400 MHz): = 7.60 (br d, J = 7.9 Hz, 2 H), 7.41 (br dd,
rahedron Lett. 2011, 52, 5149.
3
J = 7.9, 7.3 Hz, 2 H), 7.32 (dddd, J = 7.3, 7.3, 1.2, 1.2 Hz, 1 H), 7.18 (d, J =
(18) (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. (b) Luo, Y.
G.; Basha, R. S.; Reddy, D. M.; Xue, Y. J.; Chen, T. H.; Lee, C. F. Org.
Lett. 2018, 20, 6872. (c) Lessing, T.; Müller, T. J. J. Chem. Hetero-
cycl. Compd. 2018, 54, 334.
3.8 Hz, 1 H), 7.12 (d, J = 3.8 Hz, 1 H), 2.13 (s, 3 H).
13
C NMR (CDCl , 100 MHz): = 144.2, 133.7, 131.8, 128.7, 127.5,
3
123.3, 122.6, 90.6, 73.0, 4.5.
(
19) Barange, D. K.; Batchu, V. R.; Gorja, D.; Pattabiraman, V. R.;
Tatini, L. K.; Babu, J. M.; Pal, M. Tetrahedron 2007, 63, 1775.
20) Yan, B.; Fu, Y.; Zhu, H.; Chen, Z. J. Org. Chem. 2019, 84, 4246.
MS (EI): m/z (%) = 39 (4), 51 (5), 63 (5), 77 (8), 99 (5), 121 (8), 139 (5),
+
+
1
52 (10), 165 (30), 198 (100) [M] , 200 (27) [M+2] .
(
+
+
HRMS (ESI, V ): m/z [M + H] calcd for C13H11S: 199.0581; found:
99.0582.
(21) Zhao, Y.; Zhang, Z.; Liu, X.; Wang, Z.; Cao, Z.; Tian, L.; Yue, M.;
1
You, J. J. Org. Chem. 2019, 84, 1379.
(
22) (a) Birkinshaw, J. H.; Chaplen, P. Biochem. J. 1955, 60, 255.
b) Atkinson, R. E.; Curtis, R. F.; Taylor, J. A. J. Chem. Soc. C 1967,
(
Funding Information
578. (c) Carpita, A.; Lezzi, A.; Rossi, R.; Marchetti, F.; Merlino, S.
Tetrahedron 1985, 41,03 621. (d) Christensen, L. P.; Lam, J. Phy-
tochemistry 1991, 30,01 11. (e) Zhang, L.; Chen, C. J.; Chen, J.;
Zhao, Q. Q.; Li, Y.; Gao, K. Phytochemistry 2014, 106, 134.
We thank the University of Costa Rica and Vicerrectoría de Investi-
gación for financial support.()
(23) (a) Yu, H.; Richey, R. N.; Mendiola, J.; Adeva, M.; Somoza, C.;
May, S. A.; Carson, M. W.; Coghlan, M. J. Tetrahedron Lett. 2008,
Acknowledgment
49, 1915. (b) Richey, R. N.; Yu, H. Org. Process Res. Dev. 2009, 13,
3
15.
We thank Lorena Hernández of CIPRONA-UCR for high-resolution
mass determination, and Prof. Cam Oehlschlager and Dr. Albán
Pereira for reading the manuscript and for useful suggestions.
(
(
24) Sörensen, J. S.; Sörensen, N. A. Acta Chem. Scand. 1958, 12, 771.
25) Kimura, Y.; Hiraoka, K.; Kawano, T.; Fujioka, S.; Shimada, A. Z.
Naturforsch., C: J. Biosci. 2008, 63, 843.
(
(
26) Guddal, E.; Sörensen, N. A. Acta Chem. Scand. 1959, 13, 1185.
27) Hooz, J.; Cabezas, J.; Musmanni, S.; Calzada, J. Org. Synth. 1990,
Supporting Information
69, 120.
(
28) For the original report on this preparation, see: Hooz, J.;
Calzada, J. G.; McMaster, D. Tetrahedron Lett. 1985, 26,03 271.
29) Cabezas, J. A.; Alvarez, L. X. Tetrahedron Lett. 1998, 39, 3935.
30) Cabezas, J. A.; Pereira, A. R.; Amey, A. Tetrahedron Lett. 2001, 42,
Supporting information for this article is available online at
https://doi.org/10.1055/s-0039-1690895. H and C NMR spectra of
1
13
(
(
all compounds prepared in Table 2 are provided.
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o
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6819.
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(
31) Vásquez, S.; Cabezas, J. A. Tetrahedron Lett. 2014, 55, 1894.
32) Pereira, A. R.; Cabezas, J. A. J. Org. Chem. 2005, 70,07 2594.
References
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(
(
(
(
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(36) A solvent ratio (v/v) of ether/hexane of 1:1 was used, as previ-
27
ously reported.
(37) Cabezas, J. A.; Poveda, R. R.; Brenes, J. A. Synthesis 2018, 50,
3307.
(
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2020. Thieme. All rights reserved. Synthesis 2020, 52, A–H