H. Yang et al. / Tetrahedron 69 (2013) 2588e2593
2593
d
¼168.6, 135.1, 134.0, 131.2, 129.4, 120.3, 119.9, 42.6, 20.8 ppm.
Research Fund; Key laboratory Polymer Materials of Gansu Prov-
ince (Northwest Normal University); Bioactive Product Engineering
Research Center for Gansu Distinctive Plants; State Key Laboratory
of Applied Organic Chemistry, Lanzhou University.
HRMS (ESþ) calcd for C11H13NO (MþH) 176.1070, found 176.1074.
4.4.5. N-(4-Methoxyphenyl)but-3-enamide (5e). 0.31 g (80%); white
solid. 1H NMR (400 MHz, CDCl3):
d¼7.29 (d, J¼7.6 Hz, 2H), 6.84 (d,
J¼8.8, 2H), 6.73 (br, 1H), 5.99e5.91 (m, 1H), 5.34 (d, J¼16.8 Hz, 1H),
5.24 (d, J¼10.4 Hz, 1H), 4.65 (d, J¼5.6 Hz, 2H), 3.77 (s, 3H) ppm. 13C
Supplementary data
NMR (100 MHz, CDCl3):
d
¼155.9, 153.6, 132.5, 130.8, 120.6, 118.1,
Supplementary data related to this article can be found at
114.2, 65.7, 55.4 ppm. HRMS: none.
4.4.6. N-o-Tolylbut-3-enamide (5f). 0.34 g (96%); white solid. 1H
NMR (400 MHz, CDCl3):
d
¼7.86 (d, J¼8.0 Hz, 1H), 7.25e7.16 (m, 2H),
References and notes
7.07 (t, J¼7.6 Hz, 1H), 6.13e6.02 (m, 1H), 5.39e5.35 (m, 2H), 3.22 (d,
J¼6.8 Hz, 2H), 2.23 (s, 3H) ppm.13C NMR (100 MHz, CDCl3):
¼168.4,
d
1. (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53,
2390e2392; (b) Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010,
132, 4101e4103; (c) Haag, B. A.; Zhang, Z.-G.; Li, J.-S.; Knochel, P. Angew. Chem.,
Int. Ed. 2010, 49, 9513e9516; (d) Luzung, M. R.; Patel, J. S.; Yin, J. J. Org. Chem.
2010, 75, 8330e8332; (e) Manolikakes, G.; Hernandez, C. M.; Schade, M. A.;
Metzger, A.; Knochel, P. J. Org. Chem. 2008, 73, 8422e8436; (f) Yeung, C. S.;
Dong, V. M. J. Am. Chem. Soc. 2008, 130, 7826e7827.
135.5, 131.3, 130.4, 128.6, 126.8, 125.1, 122.6, 120.9, 42.6, 17.6. HRMS
(ESþ) calcd for C11H13NO (MþH) 176.1070, found 176.1072.
4.4.7. N-(Naphthalen-2-yl)but-3-enamide (5g). 0.36 g (86%); white
solid. 1H NMR (400 MHz, CDCl3):
d
¼8.19 (d, J¼1.6 Hz, 1H), 7.77
2. (a) Knochel, P. Handbook of Functˇ ionalized Organometallics; Wiley-VCH:
(d, J¼8.0 Hz, 3H), 7.61 (br,1H), 7.46e7.38 (m, 3H), 6.12e6.01 (m,1H),
ꢀ
Weinhein, Germany, 2005; (b) Lepretre, A.; Turck, A.; Ple, N.; Knochel, P.;
5.37 (s, 1H), 5.33 (d, J¼8.4 Hz, 1H), 3.23 (d, J¼7.2 Hz, 2H) ppm. 13C
ꢀ
Queguiner, G. Tetrahedron 2000, 56, 265e274; (c) Knochel, P.; Singer, R. D.
Chem. Rev. 1993, 93, 2117e2188; (d) Erdik, E. Tetrahedron 1992, 48,
9577e9648; (e) Knochel, P.; Almena Perea, J. J.; Jones, P. Tetrahedron 1998,
54, 8275e8317.
NMR (100 MHz, CDCl3):
d
¼168.9, 135.1, 133.8, 131.0, 130.1, 128.7,
127.6, 127.5, 126.5, 125.0, 120.6, 119.7, 116.6, 42.7 ppm. HRMS (ESþ)
calcd for C14H13NO (MþH) 212.1070, found 212.1067.
3. (a) Urkalan, K. B.; Sigman, M. S. J. Am. Chem. Soc. 2009, 131, 18042e18043; (b)
Hadei, N.; Achondul, G. T.; Valente, C.; O’Brien, C. J.; Organ, M. G. Angew. Chem.,
Int. Ed. 2011, 50, 3896e3899; (c) Metzger, A.; Melzig, L.; Despotopoulou, C.;
Knochel, P. Org. Lett. 2009, 11, 4228e4231; (d) Hadei, N.; Kantchev, E. A. B.;
O’Brien, C. J.; Organ, M. G. J. Org. Chem. 2005, 70, 8503e8507; (e) Zeng, X.; Qian,
M.; Hu, Q.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2259e2263; (f) Negishi, E.
Acc. Chem. Res. 1982, 15, 340e348; (g) Li, M.; Yan, X.-X.; Hong, W.; Zhu, X.-Z.;
Cao, B.-X.; Sun, J.; Hou, X.-L. Org. Lett. 2004, 6, 2833e2835; (h) Wang, D.; Zhang,
Z. Org. Lett. 2003, 5, 4645e4648.
4. (a) Melzig, L.; Metzger, A.; Knochel, P. J. Org. Chem. 2010, 75, 2131e2133; (b)
Xie, L.-G.; Wang, Z.-X. Angew. Chem., Int. Ed. 2011, 50, 4901e4904; (c) Li, B.-J.;
Li, Y.-Z.; Lu, X.-Y.; Liu, J.; Guan, B.-T.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47,
10124e10127; (d) Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127,
4.4.8. N-Phenylbut-3-ynamide (5h). 0.17 g (55%); white solid. 1H
NMR (400 MHz, CDCl3):
d¼8.21 (br, 1H), 7.54 (dd, J¼8.0, 0.8 Hz, 2H),
7.35 (t, J¼7.6 Hz, 2H), 7.15 (t, J¼7.6 Hz, 1H), 3.39 (d, J¼2.8 Hz, 2H),
2.51 (t, J¼2.4 Hz, 1H) ppm. 13C NMR (100 MHz, CDCl3):
¼164.0,
d
137.1, 129.1, 124.9, 119.9, 75.1, 28.4 ppm. HRMS (ESþ) calcd for
C10H9NO (MþH) 160.0757, found 160.0762.
4.4.9. N-(4-Methoxyphenyl)but-3-ynamide (5i). 0.16 g (43%); white
solid. 1H NMR (400 MHz, CDCl3):
d
¼8.14 (br, 1H), 7.43e7.27 (m, 2H),
~
ꢀ
4594e4595; (e) Phapale, V. B.; Bunuel, E.; García-Iglesias, M.; Cardenas, D. J.
Angew. Chem., Int. Ed. 2007, 46, 8790e8795; (f) Gavryushin, A.; Kofink, C.;
Manolikakes, G.; Knochel, P. Org. Lett. 2005, 7, 4871e4874; (g) Ochiai, H.;
Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 2681e2683.
6.89e6.86 (m, 2H), 3.82 (s, 3H), 3.36 (d, J¼2.8 Hz, 2H), 2.48
(t, J¼2.8 Hz, 1H) ppm. 13C NMR (100 MHz, CDCl3):
¼164.0, 156.8,
d
130.2, 122.0, 114.2, 74.8, 55.4, 28.1 ppm. HRMS (ESþ) calcd for
C11H11NO2 (MþH) 190.0863, found 190.0866.
ꢀ
5. (a) Esquivias, J.; Arrayas, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2007, 46,
9257e9260; (b) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799e4802;
(c) Yeh, M. C. P.; Knochel, P.; Santa, L. E. Tetrahedron Lett. 1988, 29, 3887e3890.
6. Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. 1996, 35, 1700e1701.
4.4.10. N-(4-Chlorophenyl)but-3-ynamide (5j). 0.15 g (40%); white
ꢀ
7. (a) Kazmierski, I.; Bastienne, M.; Gosmini, C.; Paris, J.-M.; Perichon, J. J. Org.
solid. 1H NMR (400 MHz, CDCl3):
d
¼8.21 (br, 1H), 7.50 (d, J¼8.8 Hz,
2H), 7.31 (d, J¼8.8 Hz, 2H), 3.39 (d, J¼2.8 Hz, 2H), 2.51 (t, J¼2.8 Hz,
1H). ppm. 13C NMR (100 MHz, CDCl3):
Chem. 2004, 69, 936e942; (b) Fillon, H.; Gosmini, C.; Perichon, J. J. Am. Chem.
Soc. 2003, 125, 3867e3870; (c) Gosmini, C.; Rollin, Y.; Nedelec, J. Y.; Perichon, J.
J. Org. Chem. 2000, 65, 6024e6026.
8. Peng, Z.-Y.; Ma, F.-F.; Zhu, L.-F.; Xie, X.-M.; Zhang, Z. J. Org. Chem. 2009, 74,
6855e6858.
9. (a) Metzger, A.; Bernhardt, S.; Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed.
2010, 49, 4665e4668; (b) Kobayashi, K.; Kondo, Y. Org. Lett. 2009, 11,
2035e2037.
10. (a) Zakarian, A.; Batch, A.; Holton, R. A. J. Am. Chem. Soc. 2003, 125, 7822e7824;
(b) Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. J. Org. Chem. 2002, 67,
3494e3498; (c) Dai, Q.; Xie, X.; Xu, S.; Ma, D.; Tang, S.; She, X. Org. Lett. 2011, 13,
2302e2305; (d) Pandey, S. K.; Ramana, C. V. J. Org. Chem. 2011, 76, 2315e2318;
(e) Petri, A. F.; Schneekloth, J. S.; Mandal, A. K.; Crews, C. M. Org. Lett. 2007, 9,
3001e3004.
11. (a) Wang, J.-X.; Fu, Y.; Hu, Y. Angew. Chem., Int. Ed. 2002, 41, 2757e2760; (b) Hu,
Y.; Yu, J.; Yang, S.; Wang, J.-X.; Yin, Y. Synlett 1998, 1213e1214; (c) Hu, Y.; Wang,
J.-X.; Li, W. Chem. Lett. 2001, 174e175; (d) Wang, J.-X.; Fu, Y.; Hu, Y.; Wang, K.
Synthesis 2003, 1506e1510; (e) Wei, Y.-J.; Ren, H.; Wang, J.-X. Tetrahedron Lett.
2008, 49, 5697e5699; (f) Wang, J.-X.; Wang, K.; Zhao, L.; Li, H.; Fu, Y.; Hu, Y. Adv.
Synth. Catal. 2006, 348, 1262e1270; (g) Huang, D.; Wang, J.-X. Synlett 2007,
2272e2276; (h) Fu, Y.; Wang, J.-X.; Wang, K.; Hu, Y. Tetrahedron 2008, 64,
11124e11128.
d
¼164.0, 135.7, 129.9, 129.7,
129.1, 121.1, 75.3, 28.3 ppm. HRMS (ESþ) calcd for C10H8ClNO
(MþH) 194.0367, found 194.0370.
4.4.11. N-p-Tolylbut-3-ynamide (5k). 0.15 g (42%); white solid. 1H
NMR (400 MHz, CDCl3):
7.15e7.09 (m, 2H), 3.36 (d, J¼2.8 Hz, 2H), 2.48 (t, J¼2.8 Hz, 1H), 2.32
(s, 3H) ppm. 13C NMR (100 MHz, CDCl3):
d¼8.17 (br, 1H), 7.41e7.26 (m, 2H),
d
¼164.0, 134.6, 129.5,
120.0, 74.9, 28.3, 20.8 ppm. HRMS (ESþ) calcd for C11H11NO (MþH)
174.0913, found 174.0917.
Acknowledgements
This work was supported by National Natural Science Founda-
tion of China (21262031); Gansu Province Universities Basic