NJC
Paper
(d, J = 9.0 Hz, 2H), 6.95 (d, J = 9.0 Hz, 2H), 3.74 (s, 3H); 13C NMR 26.3, 25.5, 24.3; HRMS (EI): calcd for C13H16N2O3 248.1161,
(100 MHz, CDCl3): d 165.1, 134.4, 132.3, 129.2, 128.4, 127.9, found 248.1158.
126.8, 114.7, 56.4, 56.1; HRMS (EI): calcd for C14H13NO2
227.0946, found 227.0943.
Compound 2q (ref. 24d). 1H NMR (400 MHz, CDCl3): d = 8.51
(br t, J = 5.1 Hz, 2H), 7.66 (d, J = 7.8 Hz, 1H), 7.30–7.23 (m, 1H),
Compound 2h (ref. 15). 1H NMR (400 MHz, CDCl3): d = 9.89 3.72 (s, 2H), 3.55 (br t, J = 5.5 Hz, 2H), 3.45 (br t, J = 5.5 Hz, 2H),
(br, 1H), 8.36 (d, J = 9.0 Hz, 2H), 7.86–7.15 (m, 5H), 8.23 (d, J = 1.66–1.60 (m, 2H), 1.57–1.50 (m, 2H), 1.47–1.40 (m, 2H); 13C
9.0 Hz, 2H); 13C NMR (100 MHz, CDCl3): d 169.4, 149.6, 141.1, NMR (100 MHz, CDCl3): d 168.3, 149.9, 148.3, 136.5, 130.6,
139.0, 128.6, 127.2, 124.2, 123.5, 120.2; HRMS (EI): calcd for 122.8, 25.3, 26.4, 37.9, 43.1, 47.1, 24.5; HRMS (EI): calcd for
C
13H10N2O3 242.0691, found 242.0693.
C12H16N2O 204.1263, found 204.1265.
Compound 2i (ref. 24a). 1H NMR (400 MHz, CDCl3): d = 6.48
(br s, 1H), 3.18–3.23 (m, 2H), 2.44–2.47 (m, 2H), 1.60–1.76 (m,
6H), 13C NMR (100 MHz, CDCl3): d 179.3, 43.0, 36.9, 30.7, 29.9,
23.3; HRMS (EI): calcd for C6H11NO 113.0841, found 113.0840.
Compound 2j (ref. 18a). 1H NMR (400 MHz, CDCl3): d = 6.29
(br, 1H), 4.00–4.14 (m, 1H), 2.30 (septet, J = 6.9 Hz, 1H), 1.18
(d, J = 6.9 Hz, 12H); 13C NMR (100 MHz, CDCl3): d 174.6, 41.6,
36.1, 23.5, 19.8; HRMS (EI): calcd for C7H15NO 129.1154, found
129.1152.
Acknowledgements
We sincerely thank the SAIF, Punjab University, Chandigarh,
for providing spectra. V.P.S. is grateful to the Department of
Science and Technology (DST) Govt. of India, for the award of a
DST-Inspire Faculty position (Ref. IFA-11CH-08) and financial
support, and A.K.Y. is grateful to the CSIR, New Delhi, for the
award of a Junior Research Fellowship.
Compound 2k (ref. 24d). 1H NMR (400 MHz, CDCl3): d = 7.35
(br t, J = 7.4 Hz, 2H), 7.34–7.21 (m, 9H), 7.21 (d, J = 7.2 Hz, 2H),
Notes and references
7.09 (d, J = 7.4 Hz, 2H), 4.60 (s, 2H), 4.45 (s, 2H), 3.77 (s, 2H); 13
C
NMR (100 MHz, CDCl3): d 171.5, 137.3, 136.3, 135.1, 128.9,
128.7, 128.5, 128.3, 128.0, 127.8, 127.4, 126.9, 126.6, 50.3, 48.2,
41.1; HRMS (EI): calcd for C22H21NO 315.1623, found 315.1620.
Compound 2l (ref. 24c). 1H NMR (400 MHz, CDCl3): d = 7.33
(t, J = 7.7 Hz, 2H), 7.30–7.19 (m, 3H), 3.73 (s, 2H), 3.60 (br t, J =
5.3 Hz, 2H), 3.38 (br t, J = 5.4 Hz, 2H), 1.59–1.53 (m, 2H),
1.50–1.48 (m, 2H), 1.35–1.33 (m, 2H); 13C NMR (100 MHz,
CDCl3); d 169.5, 135.4, 128.7, 128.4, 126.7, 47.3, 43.0, 41.1,
26.3, 25.4, 24.5; HRMS (EI): calcd for C13H17NO 203.1310, found
203.1312.
1 For leading reviews, see: (a) J. W. Tucker and C. R. J.
Stephenson, J. Org. Chem., 2012, 77, 1617; (b) J. M. R.
Narayanam and C. R. J. Stephenson, Chem. Soc. Rev., 2011,
40, 102; (c) F. Teply, Collect. Czech. Chem. Commun., 2011,
76, 859; (d) T. P. Yoon, M. A. Ischay and J. N. Du, Nat. Chem.,
2010, 2, 527; (e) K. Zeitler, Angew. Chem., Int. Ed., 2009,
48, 9785; ( f ) J. Xuan and W.-J. Xiao, Angew. Chem., Int. Ed.,
2012, 51, 6828; (g) D. Ravelli and M. Fagnoni, Chem-
CatChem, 2012, 4, 169; (h) D. Rovelli, M. Fagnoni and
A. Albini, Chem. Soc. Rev., 2013, 42, 97; (i) Y. Cheng,
J. Yang, Y. Qu and P. Li, Org. Lett., 2011, 14, 98; ( j) J. M. R.
Narayanam, J. W. Tucker and C. R. J. Stephenson, J. Am.
Chem. Soc., 2009, 131, 8756.
2 (a) R. Srinivasan, J. Am. Chem. Soc., 1963, 85, 3048;
(b) R. G. Salomon and J. K. Kochi, J. Am. Chem. Soc., 1974,
96, 1137; (c) J. K. Kochi, Angew. Chem., Int. Ed. Engl., 1988,
27, 1227.
3 D. A. Nicewicz and D. W. C. MacMillan, Science, 2008,
322, 77.
Compound 2m (ref. 24d). 1H NMR (400 MHz, CDCl3): d =
7.16–7.08 (m, 4H), 3.70 (s, 2H), 3.54 (br t, J = 5.2 Hz, 2H), 3.33
(br t, J = 5.4 Hz, 2H), 2.32 (s, 3H), 1.59–1.54 (m, 2H), 1.51–1.48
(m, 2H), 1.39–1.33 (m, 2H); 13C NMR (100 MHz, CDCl3): d 169.7,
136.1, 132.4, 129.3, 128.6, 47.3, 43.0, 40.8, 26.3, 25.6, 24.4, 21.1;
HRMS (EI): calcd for C14H19NO 217.1467, found 217.1465.
Compound 2n (ref. 24d). 1H NMR (400 MHz, CDCl3): d = 7.20
(br t, J = 7.6 Hz, 1H), 7.10 (s, 1H), 7.03 (br d, J = 7.4 Hz, 2H), 3.71
(s, 2H), 3.55 (br t, J = 5.5 Hz, 2H), 3.35 (br t, J = 5.5 Hz, 2H), 2.33
(s, 3H), 1.62–1.56 (m, 2H), 1.54–1.48 (m, 2H), 1.40–1.34 (m, 2H);
13C NMR (100 MHz, CDCl3): d 169.3, 138.4, 135.5, 129.3, 128.4,
127.4, 125.5, 47.4, 42.8, 41.1, 26.3, 25.6, 24.5, 21.3; HRMS (EI):
calcd for C14H19NO 217.1467, found 217.1469.
4 M. A. Ischay, M. E. Anzovino, J. Du and T. P. Yoon, J. Am.
Chem. Soc., 2008, 130, 12886.
5 (a) Y.-Q. Zou, J.-R. Chen, X.-P. Liu, L.-Q. Lu, R. L. Davis,
K. A. Jørgensen and W.-J. Xiao, Angew. Chem., Int. Ed., 2012,
Compound 2o (ref. 24d). 1H NMR (400 MHz, CDCl3): d = 7.18
(d, J = 8.6 Hz, 2H), 6.88 (d, J = 8.6 Hz, 2H), 3.81 (s, 3H), 3.66
(s, 2H), 3.54 (br t, J = 5.3 Hz, 2H), 3.40 (br t, J = 5.5 Hz, 2H),
1.63–1.55 (m, 2H), 1.53–1.47 (m, 2H), 1.40–1.32 (m, 2H); 13C
NMR (100 MHz, CDCl3): d 169.7, 158.2, 129.6, 127.6, 114.2, 55.3,
47.1, 43.0, 40.3, 26.2, 25.6, 24.5; HRMS (EI): calcd for
51, 784; (b) M. Neumann, S. Fu¨ldner, B. Konig and K. Zeitler,
¨
Angew. Chem., Int. Ed., 2011, 50, 951; (c) D. P. Hari and
B. Konig, Org. Lett., 2011, 13, 3852; (d) K. Fidaly, C. Ceballos,
A. Falguieres, M. S.-I. Veitia, A. Guy and C. Ferroud, Green
Chem., 2012, 14, 1293; (e) V. Rey, S. Soria-Catro,
¨
`
´´´
J. E. Arguello and A. B. Penenory, Tetrahedron Lett., 2009,
C
14H19NO2 233.1416, found 233.1415.
50, 4720.
Compound 2p (ref. 24d). 1H NMR (400 MHz, CDCl3,): d =
6 (a) J. M. Humphrey and A. R. Chamberlin, Chem. Rev., 1997,
97, 2243; (b) T. Cupido, J. Tulla-Puche, J. Spengler and
F. Alberricio, Curr. Opin. Drug Discovery Dev., 2007, 10, 768.
7 S. Abuzar, S. Sharma and R. N. Iyer, Indian J. Chem., Sect. B:
Org. Chem. Incl. Med. Chem., 1980, 19, 211.
8.20 (d, J = 8.6 Hz, 2H), 7.44 (d, J = 8.5 Hz, 2H), 3.60 (s, 2H), 3.60
(t, J = 5.5 Hz, 2H), 3.40 (t, J = 5.5 Hz, 2H), 1.65–1.60 (m, 2H),
1.58–1.50 (m, 2H), 1.46–1.40 (m, 2H); 13C NMR (100 MHz,
CDCl3): d 167.6, 147.0, 143.1, 130.0, 123.9, 47.3, 43.1, 40.6,
c
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2013
New J. Chem., 2013, 37, 4119--4124 4123