G
M. Hayakawa et al.
Paper
Synthesis
13C NMR (100 MHz, CDCl3): = 14.2, 16.5, 120.6, 123.3, 124.3, 124.4,
125.7, 128.9, 129.8, 130.3, 132.1, 133.5, 134.7, 135.6.
HRMS (APCI): m/z [M + H]+ calcd for C14H13S: 213.0737; found:
213.0732.
13C NMR (100 MHz, CDCl3): = 14.1, 16.7, 22.7, 28.7, 29.3, 29.4, 29.5,
29.6, 29.7, 29.7 (overlap), 31.6, 31.9, 120.7, 123.4, 124.3, 124.4, 125.7,
128.9, 129.2, 130.4, 132.0, 134.8, 135.8, 139.9.
HRMS (APCI): m/z [M + H]+ calcd for C31H47S: 451.3398; found:
451.3407.
2-Butyl-1-methylnaphtho[2,1-b]thiophene (6ga)
Anal. Calcd for C31H46S: C, 82.60; H, 10.29. Found: C, 82.22; H, 10.16.
Yield: 226 mg (89%); yellow crystals; mp 43–45 °C (n-hexane).
IR (neat): 2950, 1509, 1464, 1370, 798 cm–1
.
Supporting Information
1H NMR (400 MHz, CDCl3): = 0.97 (t, J = 7.5 Hz, 3 H), 1.45 (sext,
J = 7.5 Hz, 2 H), 1.72 (quint, J = 7.5 Hz, 2 H), 2.78 (s, 3 H), 2.94 (t, J = 7.5
Hz, 2 H), 7.47–7.58 (m, 2 H), 7.65 (d, J = 8.5 Hz, 1 H), 7.78 (d, J = 8.5 Hz,
1 H), 7.93 (d, J = 8.2 Hz, 1 H), 8.70 (d, J = 8.5 Hz, 1 H).
Supporting information for this article is available online at
S
u
p
p
orti
n
gInformati
o
n
S
u
p
p
orti
n
gInformati
o
n
13C NMR (100 MHz, CDCl3): = 13.9, 16.7, 22.4, 28.4, 33.7, 120.7,
123.4, 124.3, 124.4, 125.7, 128.9, 129.2, 130.4, 132.1, 134.8, 135.8,
139.8.
HRMS (APCI): m/z [M + H]+ calcd for C17H19S: 255.1207; found:
255.1217.
References
(1) Aoyama, T.; Orito, M.; Takido, T.; Kodomari, M. Synthesis 2008,
2089.
(2) (a) Acharya, A.; Kumar, S. V.; Saraiah, B.; Ila, H. J. Org. Chem.
2015, 80, 2884. (b) Tu, S.; Xie, Y. Q.; Gui, L. Y.; Huang, Z. L.;
Huang, Y. B.; Che, L. M. Bioorg. Med. Chem. Lett. 2014, 24, 2173.
(c) Matthews, J. M.; Qin, N.; Colburn, R. W.; Dax, S. L.; Hawkins,
M.; McNally, J. J.; Reany, L.; Youngman, M. R.; Baker, J.;
Hutchinson, T.; Liu, Y.; Lubin, M. L.; Neeper, M.; Brandt, M. R.;
Stone, D. J.; Flores, C. M. Bioorg. Med. Chem. Lett. 2012, 22, 2922.
(d) Singh, P. P.; Yadav, H.; Ila, H.; Junjappa, H. J. Org. Chem. 2009,
74, 5496. (e) Martorana, A.; Gentile, C.; Perricone, U.;
Piccionello, A. P.; Bartolotta, R.; Terenzi, A.; Pace, A.; Mingoia, F.;
Almerico, A. M.; Lauria, A. Eur. J. Med. Chem. 2015, 90, 537.
(f) Mesangeau, C.; Fraise, M.; Delagrange, P.; Caignard, D. H.;
Boutin, J. A.; Berthelot, P.; Yous, S. Eur. J. Med. Chem. 2011, 46,
1835. (g) Amr, A. E.; Sherif, M. H.; Assay, M. G.; Al-Omar, M. A.;
Ragab, I. Eur. J. Med. Chem. 2010, 45, 5935. (h) Fakhr, I. M. I.;
Radwan, M. A. A.; El-Batran, S.; El-Salam, O. M. E. A.; El-Shen-
awy, S. M. Eur. J. Med. Chem. 2009, 44, 1718.
Anal. Calcd for C17H18S: C, 80.26; H, 7.13. Found: C, 80.56; H, 7.16.
1-Methyl-2-octylnaphtho[2,1-b]thiophene (6ha)
Yield: 273 mg (88%); colorless needles; mp 54–55 °C (n-hexane).
IR (neat): 2927, 2851, 1465, 802, 733 cm–1
.
1H NMR (400 MHz, CDCl3): = 0.88 (t, J = 7.1 Hz, 3 H), 1.23–1.46 (m,
10 H), 1.73 (quint, J = 7.8 Hz, 2 H), 2.78 (s, 3 H), 2.94 (t, J = 7.8 Hz, 2 H),
7.47–7.58 (m, 2 H), 7.65 (d, J = 8.5 Hz, 1 H), 7.78 (d, J = 8.2 Hz, 1 H),
7.93 (d, J = 8.2 Hz, 1 H), 8.72 (d, J = 8.5 Hz, 1 H).
13C NMR (100 MHz, CDCl3): = 14.1, 16.7, 22.7, 28.7, 29.3, 29.3, 29.4,
31.6, 31.9, 120.7, 123.4, 124.3, 124.4, 125.7, 128.9, 129.2, 130.4, 132.1,
134.8, 135.8, 139.9.
HRMS (APCI): m/z [M + H]+ calcd for C21H27S: 311.1827; found:
311.1827.
Anal. Calcd for C21H26S: C, 81.23; H, 8.44. Found: C, 81.36; H, 8.42.
(3) Sashida, H.; Sadamori, K.; Tsuchiya, T. Synth. Commun. 1998, 28,
713.
2-Dodecyl-1-methylnaphtho[2,1-b]thiophene (6ia)
(4) (a) Wang, Y.; Parkin, S. R.; Watson, M. D. Org. Lett. 2008, 10,
4421. (b) Kashiki, T.; Shinamura, S.; Kohara, M.; Miyazaki, E.;
Takimiya, K.; Ikeda, M.; Kuwabara, H. Org. Lett. 2009, 11, 2473.
(5) (a) Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem. Int. Ed.
2006, 45, 4473. (b) Yamauchi, T.; Shibahara, F.; Murai, T. Tetra-
hedron Lett. 2016, 57, 2945. (c) Huang, H.; Dang, P.; Wu, Y. L.;
Liu, J. Tetrahedron Lett. 2016, 57, 574.
Yield: 297 mg (81%); colorless needles; mp 69–71 °C (n-hexane).
IR (neat): 2915, 1466, 802, 733 cm–1
.
1H NMR (400 MHz, CDCl3): = 0.88 (t, J = 6.9 Hz, 3 H), 1.26–1.45 (m,
18 H), 1.73 (quint, J = 7.6 Hz, 2 H), 2.78 (s, 3 H), 2.94 (t, J = 7.6 Hz, 2 H),
7.48–7.59 (m, 2 H), 7.65 (d, J = 8.5 Hz, 1 H), 7.79 (d, J = 8.5 Hz, 1 H),
7.93 (d, J = 8.1 Hz, 1 H), 8.72 (d, J = 8.5 Hz, 1 H).
13C NMR (100 MHz, CDCl3): = 14.1, 16.7, 22.7, 28.7, 29.3, 29.4, 29.5,
29.6, 29.7, 29.7, 29.7, 31.5, 31.9, 120.7, 123.4, 124.3, 124.4, 125.7,
128.9, 129.2, 130.4, 132.0, 134.8, 135.8, 139.9.
(6) Jingwen, C.; Haifeng, X.; Li, Y.; Xiangge, Z. RSC Adv. 2017, 7,
7753.
(7) (a) Aoyama, T.; Murata, S.; Takido, T.; Kodomari, M. Tetrahedron
2007, 63, 11933. (b) Sakai, H.; Tsutsumi, K.; Morimoto, T.;
Kakiuchi, K. Adv. Synth. Catal. 2008, 350, 2498. (c) Maheswari, S.
U.; Perumal, S. Tetrahedron Lett. 2012, 53, 6885. (d) Dalvi, P. B.;
Lin, S. F.; Paike, V.; Sun, C. M. ACS. Comb. Sci. 2015, 17, 421.
(e) Aoyama, T.; Yamamoto, T.; Miyota, S.; Hayakawa, M.; Takido,
T.; Kodomari, M. Synlett 2014, 25, 1571. (f) Aoyama, T.; Nagaoka,
T.; Takido, T.; Kodomari, M. Synthesis 2011, 619.
(8) (a) Daub, G. W.; Zuckermann, R. N. J. Org. Chem. 1985, 50, 1599.
(b) Steward, K. M.; Corbett, M. T.; Goodman, C. G.; Johnson, J. S.
J. Am. Chem. Soc. 2012, 134, 20197.
(9) (a) Aoyama, T.; Takido, T.; Kodomari, M. Tetrahedron 2004, 45,
1873. (b) Aoyama, T.; Kubota, S.; Takido, T.; Kodomari, M. Chem.
Lett. 2011, 40, 484.
HRMS (APCI): m/z [M + H]+ calcd for C25H35S: 367.2459; found:
367.2451.
Anal. Calcd for C25H34S: C, 81.91; H, 9.35. Found: C, 81.76; H, 9.46.
1-Methyl-2-octadecylnaphtho[2,1-b]thiophene (6ja)
Yield: 342 mg (76%); white solid; mp 84–85 °C (n-hexane).
IR (neat): 2953, 1466, 802, 734 cm–1
.
1H NMR (400 MHz, CDCl3): = 0.88 (t, J = 6.6 Hz, 3 H), 1.25–1.44 (m,
30 H), 1.73 (quint, J = 7.6 Hz, 2 H), 2.78 (s, 3 H), 2.94 (t, J = 7.8 Hz, 2 H),
7.47–7.59 (m, 2 H), 7.65 (d, J = 8.5 Hz, 1 H), 7.78 (d, J = 8.5 Hz, 1 H),
7.93 (d, J = 7.8 Hz, 1 H), 8.72 (d, J = 8.5 Hz, 1 H).
(10) Chakraborti, A. A.; Gulhane, R. Chem. Commun. 2003, 71, 1896.
(11) Zolfigol, M. A. S. Tetrahedron 2001, 57, 9509.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2019, 51, A–G