7 (a) P. Magnus, D. Parry, T. Iliadis, S. A. Eisenbeis and R. A. Fairhurst,
J. Chem. Soc., Chem. Commun., 1994, 1543; (b) P. Magnus, S. Fortt,
T. Pitterna and J. P. Snyder, J. Am. Chem. Soc., 1990, 112, 4986.
8 (a) L. Banfi and G. Guanti, Angew. Chem., Int. Ed. Engl., 1995, 34,
2393; (b) K. C. Nicolaou, E. J. Sorensen, R. Discordia, C.-K. Hwang,
R. E. Minto, K. N. Bharucha and R. G. Bergman, Angew. Chem., Int.
Ed. Engl., 1992, 31, 1044; (c) A. Basak, U. K. Khamrai and
U. K. Mallick, Chem. Commun., 1996, 749.
9 (a) P. Magnus, R. T. Lewis and J. C. Huffman, J. Am. Chem. Soc.,
1988, 110, 6921; (b) P. Magnus, S. Fortt, T. Pitterna and J. P. Snyder,
J. Am. Chem. Soc., 1990, 112, 4986; (c) P. Magnus and R. A. Fairhurst,
J. Chem. Soc., Chem. Commun., 1994, 1541; (d) D. K. Moss, J. D. Spence
and M. H. Nantz, J. Org. Chem., 1999, 64, 4339; (e) M. H. Nantz,
D. K. Moss, J. D. Spence and M. M. Olmstead, Angew. Chem., Int. Ed.,
1998, 37, 47.
CCH2CH2), 1.95–1.82 (m, 2H; CH2CH2N); HRMS (ES+) calcd for
C15H13N3 (MH+) 236.1185, found 236.1201; For 3: dH (200 MHz,
CDCl3) 7.47–7.38 (m, 2H; Ar–H), 7.31–7.20 (m, 2H; Ar–H), 5.96–5.85
(m, 1H; CH2CH), 5.48 (dd, 3J (H,H) = 1.8, 16.9 Hz, 1H; CH2CHCH2),
5.18 (dd, 3J (H,H) = 1.8, 10.0 Hz, 1H; CH2CHCH2), 4.17 (s, 2H;
CH2N), 3.25 (t, 3J (H,H) = 2.4 Hz, 2H; CCH2CH); HRMS (ES+) calcd
for C14H11N3 (MH+) 222.1029, found 222.1011; For 4: dH (200 MHz,
CDCl3) 5.94–5.74 (m, 1H; CHCH2), 5.38 (qd, 3J (H,H) = 1.8, 18.6 Hz,
1H; CH2CHCH2), 5.13 (qd, 3J (H,H) = 1.8, 10.0 Hz, 1H; CH2CHCH2),
4.09 (d, 3J (H,H) = 1.4 Hz, 2H; CH2N), 3.19–3.15 (m, 2H; CCH2CH);
HRMS (ES+) calcd for C10H9N3 (MH+) 172.0873, found 172.0880; For
22: dH (500 MHz, CDCl3) 7.46 (d, 3J (H,H) = 8.5 Hz, 1H; Ar–H), 7.28–
7.06 (m, 2H; Ar–H), 7.05 (d, 3J (H,H) = 6.4 Hz, 1H; Ar–H), 5.05 (d, 3J
(H,H) = 18.3 Hz, 1H; CCH2N), 4.72–4.66 (m, 1H; NCH2CH), 4.06 (d,
3J (H,H) = 18.3 Hz, 1H; CCH2N), 3.61 (t, 3J (H,H) = 9.2 Hz, 1H;
NCH2CH), 3.36 (dd, 3J (H,H) = 2.4, 18.0 Hz, 1H; CCH2CH), 3.27 (t, 3J
(H,H) = 9.2 Hz, 1H; NCH2CH), 2.79 (dd, 3J (H,H) = 4.4, 18.0 Hz, 1H;
CCH2CH); HRMS (ES+) calcd for C14H11N (MH+) 194.0967, found
10 A. Basak and S. C. Ghosh, Tetrahedron Lett., 2005, 46, 7385.
11 R. Pal and A. Basak, Chem. Commun., 2006, 2992.
12 (a) J. J. Young and C. K. Sha, Heterocycles, 1984, 22, 2571; (b) R. Fusco,
L. Garanti and G. Zecchi, J. Org. Chem., 1975, 40, 1906; (c) Z.-Y. Chen
and M.-J. Wu, Org. Lett., 2005, 7, 475; (d) K. B. Sharpless, V. V. Fokin,
L. G. Green and V. V. Rostovtsev, Angew. Chem., Int. Ed., 2002, 41,
2596; (e) J. K. Cha, R. B. Bannett, III, J.-R. Choi and
W. D. Montgomery, J. Am. Chem. Soc., 1989, 111, 2580; (f)
J. G. Buchanan, A. R. Edgar and B. D. Hewitt, J. Chem. Soc.,
Perkin Trans. 1, 1987, 2371; (g) S. M. Weinreb, G. T. Anderson and
J. R. Henry, J. Org. Chem., 1991, 56, 6946.
3
194.1044; For 27: dH (200 MHz, CDCl3) 8.06 (s, 1H; NH), 7.34 (d, J
3
(H,H) = 8.0 Hz, 1H; Ar–H), 7.07 (d, J (H,H) = 8.0 Hz, 1H; Ar–H),
7.01 (d, 3J (H,H) = 8.0 Hz, 1H; Ar–H), 6.03–5.86 (m, 1H; CHCH2), 5.10
(s, 2H; CH2N), 5.05–5.00 (m, 1H; CHCH2), 4.92 (d, 3J (H,H) = 1.6 Hz,
1H; CHCH2), 3.52 (d, 3J (H,H) = 6.2 Hz, 2H; CCH2CH); HRMS
(ES+) calcd for C10H11N (MH+) 146.0967, found 146.1026.
15 Synthesis of allylacetylenes from terminal acetylenes and allyl halides.
N. A. Bumagin, A. B. Ponomarev and I. P. Beletskaya, Izv. Akad. Nauk
SSSR, Ser. Khim., 1987, 7, 1565 (in Russian).
13 (a) K. Sonogashira, Y. Tohoda and N. Hagihara, Tetrahedron Lett.,
1975, 16, 4467; (b) S. Takahashi, Y. Kuroyama, K. Sonogashira and
N. Hagihara, Synthesis, 1980, 627.
16 The chemical shift of NH proton for naphtho[1,8-de][1,2,3]triazine has
been reported to be d 13.29 in d6-DMSO see H. Al-Awadi,
M. R. Ibrahim, H. H. Dib, N. A. Al-Awadi and Y. A. Ibrahim,
Tetrahedron, 2005, 61, 10507.
14 Selected spectral data: For 1: dH (200 MHz, CDCl3) 8.25 (dd, 3J (H,H) =
3
1.6, 7.8 Hz, 1H; Ar–H), 7.60 (dd, J (H,H) = 1.4, 7.8 Hz, 1H; Ar–H),
7.43-7.12 (m, 2H; Ar–H), 6.62–6.48 (m, 1H; CHCH2), 5.87–5.54 (m, 1H;
CHCH2), 5.34 (dd, 3J (H,H) = 2.2, 10.4 Hz, 1H; CHCH2), 3.54–3.44 (m,
2H; CH2N), 2.80–2.63 (m, 2H; CH2CH2N); HRMS (ES+) calcd for
C14H11N3 (MH+) 222.1029, found 222.1046; For 2: dH (200 MHz,
CDCl3) 7.45–7.35 (m, 2H; Ar–H), 7.29–7.20 (m, 2H; Ar–H), 6.07 (dd, 3J
(H,H) = 11.0, 17.5 Hz, 1H; CHCH2), 5.75 (dd, 3J (H,H) = 2.2, 17.5 Hz,
1H; CHCH2), 5.58 (dd, 3J (H,H) = 2.2, 11.0 Hz, 1H; CHCH2), 3.54 (t,
3J (H,H) = 6.7 Hz, 2H; CH2N), 2.59 (t, 3J (H,H) = 6.8 Hz, 2H;
17 (a) S. Roper, M. H. Franz, R. Wartchow and H. M. R. Hoffman, Org.
Lett., 2003, 5, 2773; (b) C. von Riesen and H. M. R. Hoffman, Chem.–
Eur. J., 1996, 2, 680.
18 (a) R. Nagata, H. Yamanaka, E. Okazaki and I. Saito, Tetrahedron
Lett., 1989, 30, 4995; (b) A. G. Myers, E. Y. Kuo and N. S. Finnney,
J. Am. Chem. Soc., 1989, 111, 8057; (c) A. G. Myers and P. S. Dragovich,
J. Am. Chem. Soc., 1989, 111, 9130; (d) R. Nagata, H. Yamanaka,
E. Murahashi and I. Saito, Tetrahedron Lett., 1990, 31, 2907.
624 | Chem. Commun., 2007, 622–624
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