E.P.J. Ng et al. / Tetrahedron 67 (2011) 7728e7737
7737
ESIHRMS: found: m/z 352.1456. Calcd for C23H18N3O: (MþH)þ
8. (a) Nair, V.; George, T. G. Tetrahedron Lett. 2000, 41, 3199; (b) Gilchrist, T. L.;
Mendonc¸ a, R. Synlett 2000, 1843; (c) Palacios, F.; Aparicio, D.; de los Santos, J.
M.; Perez de Heredia, I.; Rubiales, G. Org. Prep. Proced. Int. 1995, 27, 171.
352.1450.
ꢁ
9. For recent reviews on the synthesis of pyrroles, see: (a) Estevez, V.; Villacampa,
ꢁ
M.; Menendez, J. C. Chem. Soc. Rev. 2010, 39, 4402; (b) Ferreira, V. F.; de Souza,
4.4.14. Ethyl 5-methyl-1-(1-phenylvinyl)-1H-1,2,3-triazole-4-
M.; Cunha, A. C.; Pereira, L. O. R.; Ferreira, M. L. G. Org. Prep. Proced. Int. 2001, 33,
carboxylate (7oe). Colorless oil; IR (NaCl) 2982, 2935, 1715, 1643,
ꢂ
411; (c) Genevieve, B. Angew. Chem., Int. Ed. 2004, 43, 6238; (d) Joshi, U.;
1571 cmꢁ1; 1H NMR (400 MHz, CDCl3)
d
1.43 (3H, t, J¼7.1 Hz), 2.34
Pipelier, M.; Naud, S.; Dubreuil, D. Curr. Org. Chem. 2005, 9, 261; (e) Patil, N. T.;
Yamamoto, Y. Arkivoc 2007, 10, 121; (f) Schmuck, C.; Rupprecht, D. Synthesis
2007, 3095.
(3H, s), 4.45 (2H, q, J¼7.1 Hz), 5.59 (1H, d, J¼1.1 Hz), 6.04 (1H, d,
J¼1.1 Hz), 7.12e7.15 (2H, m), 7.34e7.39 (3H, m); 13C NMR (100 MHz,
10. For recent selected reports on the synthesis of polysubstituted pyrroles, see: (a)
Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585; (b)
Morin, M. A. T.; St-Cyr, D. J.; Arndtsen, B. A. Org. Lett. 2010, 12, 4916; (c) Wang,
H.-Y.; Mueller, D. S.; Sachwani, R. M.; Londino, H. N.; Anderson, L. L. Org. Lett.
2010, 12, 2290; (d) Saito, A.; Konishi, T.; Hanzawa, Y. Org. Lett. 2010, 12, 372; (e)
Zhao, X.; Zhang, E.; Tu, Y.-Q.; Zhang, Y.-Q.; Yuan, D.-Y.; Cao, K.; Fan, C.-A.; Zhang,
F.-M. Org. Lett. 2009, 11, 4002; (f) Fu, X.; Chen, J.; Li, G.; Liu, Y. Angew. Chem., Int.
Ed. 2009, 48, 5500; (g) Lu, Y.; Arndtsen, B. A. Org. Lett. 2009, 11, 1369; (h) Liu, W.;
Jiang, H.; Huang, L. Org. Lett. 2009, 12, 312; (i) Kiren, S.; Hong, X.; Leverett, C. A.;
Padwa, A. Org. Lett. 2009, 11, 1233; (j) Fontaine, P.; Masson, G.; Zhu, J. Org. Lett.
2009, 11, 1555; (k) Davies, P. W.; Martin, N. Org. Lett. 2009, 11, 2293; (l) Aponick,
A.; Li, C.-Y.; Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624; (m) Mizuno, A.;
Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2009, 48, 8318; (n) Ackermann,
L.; Sandmann, R.; Kaspar, L. T. Org. Lett. 2009, 11, 2031; (o) Lu, Y.; Arndtsen, B. A.
Angew. Chem., Int. Ed. 2008, 47, 5430; (p) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett.
2008, 10, 2629; (q) Attanasi, O. A.; Favi, G.; Filippone, P.; Giorgi, G.; Mantellini,
F.; Moscatelli, G.; Spinelli, D. Org. Lett. 2008, 10, 1983; (r) St. Cyr, D. J.; Arndtsen,
B. A. J. Am. Chem. Soc. 2007, 129, 12366; (s) Cadierno, V.; Gimeno, J.; Nebra, N.
Chem.dEur. J. 2007, 13, 9973; (t) Su, S.; Porco, J. A., Jr. J. Am. Chem. Soc. 2007, 129,
7744; (u) Martín, R.; Rodríguez Rivero, M.; Buchwald, S. L. Angew. Chem., Int. Ed.
2006, 45, 7079; (v) Crawley, M. L.; Goljer, I.; Jenkins, D. J.; Mehlmann, J. F.;
Nogle, L.; Dooley, R.; Mahaney, P. E. Org. Lett. 2006, 8, 5837; (w) Hiroya, K.;
Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349;
(x) Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151; (y) Gorin, D. J.; Davis, N. R.;
Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
CDCl3) d 9.9, 28.0, 115.3, 125.7, 129.2, 130.1, 134.2, 138.2, 141.8, 143.6,
162.5, 194.5; ESIHRMS: found: m/z 258.1240. Calcd for C14H16N3O2:
(MþH)þ 258.1243.
4.4.15. 2,2-Dimethyl-1-(5-methyl-1-(1-phenylvinyl)-1H-1,2,3-
triazol-4-yl)propan-1-one (7of). Colorless oil; IR (NaCl) 3003, 2932,
1728, 1713, 1566, 1447 cmꢁ1; 1H NMR (400 MHz, CDCl3)
d 1.64 (9H,
s), 2.32 (3H, s), 5.58 (1H, d, J¼1.0 Hz), 6.03 (1H, d, J¼1.0 Hz),
7.14e7.16 (2H, m), 7.35e7.39 (3H, m); 13C NMR (100 MHz, CDCl3)
d
9.9, 28.0, 115.3, 125.7, 129.2, 130.1, 134.2, 138.2, 141.8, 143.6, 162.5,
194.5; ESIHRMS: found: m/z 286.1559. Calcd for C16H20N3O2:
(MþH)þ 286.1556.
4.4.16. Ethyl 5-phenyl-1-(1-phenylvinyl)-1H-1,2,3-triazole-4-
carboxylate (7og). Yellow crystal; mp 131.0e131.8 ꢀC; IR (NaCl)
3015, 1724, 1641, 1560, 1491 cmꢁ1; 1H NMR (400 MHz, CDCl3)
d 1.32
(3H, t, J¼7.1 Hz), 4.36 (2H, q, J¼7.1 Hz), 5.54 (1H, d, J¼1.2 Hz), 5.85
(1H, d, J¼1.2 Hz), 7.03e7.05 (2H, m), 7.20e7.33 (8H, m); 13C NMR
(100 MHz, CDCl3) d 14.0, 61.0, 115.5, 125.4, 125.6, 127.9, 128.5, 129.4,
11. (a) Moody, C. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley,
S., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 21; (b) Smolinsky, G.; Pryde, C. A. J.
129.5, 125.6, 134.4, 136.3, 141.5, 142.0, 160.7; ESIHRMS: found: m/z
320.1401. Calcd for C19H18N3O2: (MþH)þ 320.1399.
ꢁ
Org. Chem. 1968, 33, 2411; (c) L’abbe, G. Angew. Chem., Int. Ed. Engl. 1975, 14, 775;
(d) Hemetsberger, H.; Knittle, D.; Weidmann, H. Monatsh. Chem. 1970, 101, 161;
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Acknowledgements
12. Fe(II)- and Rh(II)-catalyzed indole formation from azidocinnamates was re-
ported, see: (a) Bonnamour, J.; Bolm, C. Org. Lett. 2011, 13, 2012; (b) Stokes, B. J.;
Dong, H.; Lesile, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129,
7500.
13. It was also found that the reaction of vinyl azides with 1,3-dicarbonyl com-
pounds in the presence of Cu(II) or Mn(III) catalysts provided pyrroles bearing
the different substitution pattern via totally distinct reaction mechanisms, see:
(a) Ng, E. P. J.; Wang, Y.-F.; Chiba, S. Synlett 2011, 783; (b) Wang, Y.-F.; Toh, K. K.;
Chiba, S.; Narasaka, K. Org. Lett. 2008, 10, 5019; (c) Chiba, S.; Wang, Y.-F.;
Lapointe, G.; Narasaka, K. Org. Lett. 2008, 10, 313.
This work was supported by funding from Nanyang Techno-
logical University and Singapore Ministry of Education, Singapore
Ministry of Education, and Science & Engineering Research Council
(A*STAR Grant No. 082 101 0019). We thank Dr. Yongxin Li (Division
of Chemistry and Biological Chemistry, School of Physical and
Mathematical Sciences, Nanyang Technological University) for as-
sistance in X-ray crystallographic analysis.
14. For reports on In(III)-catalyzed reduction of esters and amides to the corre-
sponding ethers and amines with hydrosilanes, see: (a) Sakai, N.; Moriya, T.;
Fujii, T.; Konakahara, T. Synthesis 2008, 3533; (b) Sakai, N.; Fujii, T.; Konakahara,
T. Tetrahedron Lett. 2008, 49, 6873; (c) Sakai, N.; Moriya, T.; Konakahara, T. J. Org.
Chem. 2007, 72, 5920.
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Peng, W.; Zhu, S. Synlett 2003, 187; (c) Peng, W.; Zhu, S. Tetrahedron Lett. 2003,
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