880
R. Mukherjee, A. Basak
LETTER
HRMS: m/z calcd for C28H24N2O2S + H+: 517.1433; found:
517.1440.
References and Notes
Compound 21a: 1H NMR (400 MHz, CD3COCD3): d = 10.7
(br s, 1 H), 10.0 (br s, 1 H), 8.16 (s, 1 H), 8.14 (s, 1 H), 7.67–
7.66 (m, 1 H), 7.57 (d, J = 8.0 Hz, 1 H), 7.49 (d, J = 8.4 Hz,
1 H), 7.37 (t, J = 7.6 Hz, 1 H), 7.30 (d, J = 8.0 Hz, 1 H),
7.23–7.18 (m, 2 H), 7.07 (t, J = 7.6 Hz, 1 H), 4.64 (s, 2 H),
4.39, 4.33 (ABq, J = 16.0 Hz, 2 H). 13C NMR (100 MHz,
CD3COCD3): d = 140.7, 139.3, 137.0, 129.0, 126.5, 126.2,
125.1, 123.3, 123.2, 123.1, 122.2, 120.4, 120.0, 119.5,
119.3, 116.8, 116.3, 112.1, 111.5, 110.2, 57.3, 56.7. HRMS:
m/z calcd for C22H16N2O2S + H+: 373.1011; found:
373.1014.
(1) (a) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102,
4303. (b) Chakraborty, D. P. In The Alkaloids, Vol. 44;
Cordell, G. A., Ed.; Academic Press: New York, 1993, 257;
and references cited therein. (c) Knölker, H.-J. Curr. Org.
Synth. 2004, 1, 309. (d) Knölker, H.-J. Top. Curr. Chem.
2005, 244, 115. (e) Knölker, H. J.; Reddy, K. R. In The
Alkaloids, Vol. 65; Cordell, G. A., Ed.; Academic Press:
Amsterdam, 2008, 1. (f) Jana, A. K.; Mal, D. Chem.
Commun. 2010, 46, 4411.
(2) Irlinger, B.; Bartsch, A.; Kramer, H.-J.; Mayser, P.; Steglich,
W. Helv. Chim. Acta 2005, 88, 1472.
(3) Gupta, A. K.; Bluhm, R.; Summerbell, R. J. Eur. Acad.
Dermatol. Venereol. 2002, 16, 19.
Compound 18b: 1H NMR (400 MHz, CDCl3): d = 8.00 (s, 1
H), 7.90–7,88 (m, 1 H), 7.62 (s, 1 H), 7.27–7.18 (m, 4 H),
7.09 (d, J = 6.4 Hz, 1 H), 4.64, 4.58 (ABq, J = 15.6 Hz, 2 H),
4.50, 4.47 (ABq, J = 6.8 Hz, 2 H), 4.31, 4.14 (ABq, J = 16.4
Hz, 2 H), 3.71–3.63 (m, 1 H), 2.99–2.91 (m, 1 H), 2.72 (s, 3
H), 2.45 (s, 3 H), 1.46 (t, J = 6.8 Hz, 3 H), 0.73 (t, J = 7.2 Hz,
3 H). 13C NMR (100 MHz, CDCl3): d = 153.6, 150.5, 138.7,
138.5, 134.7, 130.5, 130.4, 128.8, 126.5, 126.2, 126.0,
124.6, 124.1, 124.0, 123.1, 122.4, 117.8, 117.5, 117.0,
116.6, 116.0, 64.1, 63.7, 57.5, 56.9, 22.0, 19.2, 14.2, 12.9.
HRMS: m/z calcd for C30H28N2O6S + H+: 545.1746; found:
545.1749.
(4) Forke, R.; Jager, A.; Knölker, H.-J. Org. Biomol. Chem.
2008, 6, 2481.
(5) (a) Agenet, N.; Buisine, O.; Slowinski, F.; Gandon, V.;
Aubert, C.; Malacria, M. Org. React. 2007, 68, 1.
(b) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984,
23, 539.
(6) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644.
(7) (a) Jones, R. G.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94,
660. (b) Bergman, R. G. Acc. Chem. Res. 1973, 6, 25.
(c) Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981,
103, 4091. (d) Nicolaou, K. C.; Zuccarello, G.; Oogawa, Y.;
Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988,
110, 4866.
(8) Cycloaddition Reactions in Organic Synthesis; Kobayashi,
S.; Jorgensen, K. A., Eds.; Wiley-VCH: New York, 2002.
(9) (a) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I.
Tetrahedron Lett. 1989, 30, 4995. (b) Myers, A. G.; Kuo, E.
Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057.
(c) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989,
111, 9130. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.;
Saito, I. Tetrahedron Lett. 1990, 31, 2907.
(10) (a) Braverman, S.; Segev, D. J. Am. Chem. Soc. 1974, 96,
1245. (b) Garratt, P. J.; Neoh, S. B. J. Org. Chem. 1979, 44,
2667. (c) Cheng, Y. S. P.; Garratt, P. J.; Neoh, S. B.;
Rumjanek, V. H. Isr. J. Chem. 1985, 26, 101.
(d) Braverman, S.; Duar, Y.; Segev, D. Tetrahedron Lett.
1976, 17, 3181. (e) Zafrani, Y.; Gottlieb, H. E.; Sprecher,
M.; Braverman, S. J. Org. Chem. 2005, 70, 10166.
(11) (a) Maji, M.; Mallick, D.; Mondal, S.; Anoop, A.; Bag, S. S.;
Basak, A.; Jemmis, E. D. Org. Lett. 2011, 13, 888.
(b) Mondal, S.; Maji, M.; Basak, A. Tetrahedron Lett. 2011,
52, 1183. (c) Addy, P. S.; Dutta, S.; Biradha, K.; Basak, A.
Tetrahedron Lett. 2012, 53, 19.
(12) The indole nitrogen had to be protected due to the instability
of 3-iodoindole under Pd(0)-catalyzed reaction conditions.
(13) (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron
Lett. 1975, 16, 4467. (b) Takahashi, K.; Kuroyama, Y.;
Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
(14) CCDC 848846 contains the crystallographic data for this
paper.
Compound 21b: 1H NMR (400 MHz, CD3COCD3): d = 10.6
(br s, 1 H), 9.89 (br s, 1 H), 8.12 (s, 1 H), 7.99 (d, J = 8.4 Hz,
1 H), 7.64–7.63 (m, 1 H), 7.23–7.10 (m, 3 H), 7.05–6.95 (m,
2 H), 4.65, 4.60 (ABq, J = 15.2 Hz, 2 H), 4.37, 4.24 (ABq,
J = 15.6 Hz, 2 H), 2.61 (s, 3 H), 2.42 (s, 3 H). 13C NMR (100
MHz, CD3COCD3): d = 139.7, 139.3, 136.2, 128.8, 126.7,
126.2, 124.6, 123.6, 123.9, 122.6, 122.5, 121.1, 120.7,
120.0, 119.4, 117.7, 116.9, 116.0, 110.4, 57.1, 56.6, 16.3,
16.1. HRMS: m/z calcd for C24H20N2O2S + H+: 401.1324;
found: 401.1317.
Compound 11c: 1H NMR (400 MHz, CDCl3): d = 7.99 (d,
J = 8.8 Hz, 2 H), 7.78 (s, 2 H), 7.09 (d, J = 2.0 Hz, 2 H), 6.95
(dd, J = 2.0 Hz, 2 H), 4.50–4.43 (m, 8 H), 3.79 (s, 6 H), 1.45
(t, J = 7.2 Hz, 6 H). 13C NMR (100 MHz, CDCl3): d = 156.9,
150.3, 131.3, 130.3, 129.2, 116.3, 114.9, 102.3, 102.2, 80.8,
80.1, 63.9, 55.8, 45.3, 14.5. HRMS: m/z calcd for
C30H28N2O8S + H+: 577.1645; found: 577.1649.
Compound 18c: 1H NMR (400 MHz, CDCl3): d = 8.16 (d,
J = 8.4 Hz, 1 H), 8.00 (d, J = 9.2 Hz, 1 H), 7.96 (s, 1 H), 7.60
(s, 1 H), 7.46 (dd, J = 2.4 Hz, 1 H), 7.11 (dd, J = 2.4 Hz, 1
H), 7.02 (dd, J = 2.4 Hz, 1 H), 6.69 (dd, J = 2.4 Hz, 1 H),
4.60 (s, 2 H), 4.54–4.49 (m, 2 H), 4.46, 4.33 (ABq, J = 16.4
Hz, 2 H), 3.94 (s, 3 H), 3.76–3.72 (m, 4 H), 3.40–3.36 (m, 1
H), 1.48 (t, J = 7.2 Hz, 3 H), 0.80 (t, J = 7.2 Hz, 3 H). 13
C
NMR (100 MHz, CDCl3): d = 156.8, 156.7, 151.5, 150.9,
138.2, 134.6, 130.9, 130.0, 129.7, 128.4, 126.7, 125.5,
123.5, 120.1, 119.1, 117.1, 116.6, 116.4, 116.2, 114.7,
103.2, 102.4, 63.8, 63.4, 57.7, 57.6, 56.1, 55.9, 14.6, 13.8.
HRMS: m/z calcd for C30H28N2O8S + H+ 577.1645; found:
577.1649.
Compound 21c: 1H NMR (400 MHz, CD3COCD3): d = 10.6
(br s, 1 H), 9.9 (br s, 1 H), 8.09 (s, 1 H), 7.35 (d, J = 2.0 Hz,
1 H), 7.61 (d, J = 1.6 Hz, 1 H), 7.44 (t, J = 9.2 Hz, 2 H), 7.03
(dd, J = 2.4 Hz, 1 H), 6.86 (dd, J = 2.4 Hz, 1 H), 6.77 (d,
J = 2.0 Hz, 1 H), 4.60 (s, 2 H), 4.43, 4.34 (ABq, J = 15.6 Hz,
2 H), 3.88 (s, 3 H), 3.66 (s, 3 H). 13C NMR (100 MHz,
CD3COCD3): d = 154.8, 154.2, 139.8, 135.5, 132.0, 128.7,
126.8, 125.5, 125.4, 123.5, 123.2, 122.6, 116.9, 116.2,
115.7, 112.9, 112.8, 112.2, 110.0, 102.9, 100.8, 57.2, 56.7,
55.4, 55.1. HRMS: m/z calcd for C24H20N2O4S + H+:
433.1222; found: 433.1227.
(15) All compounds were characterized by NMR and MS
analysis.
Spectral Data of Selected Compounds
Compound 18a: 1H NMR (400 MHz, CDCl3): d = 8.30 (d,
J = 8.0 Hz, 1 H), 8.08 (d, J = 8.4 Hz, 1 H), 8.03 (s, 1 H), 8.01
(s, 1 H), 7.64 (s, 1 H), 7.55–7.51 (m, 1 H), 7.44–7.41 (m, 1
H), 7.28–7.27 (2 H, m), 4.62 (s, 2 H), 4.57–4.52 (m, 2 H),
4.45, 4.31 (ABq, J = 16.0 Hz, 2 H), 3.75–3.69 (m, 1 H),
3.30–3.25 (m, 1 H), 1.49 (t, J = 5.2 Hz, 3 H), 0.75 (t, J = 7.2
Hz, 3 H). 13C NMR (100 MHz, CDCl3): d = 151.2, 150.6,
139.9, 137.5, 135.2, 130.6, 128.6, 128.1, 128.0, 126.5,
125.4, 124.3, 123.6, 123.5, 122.7, 119.9, 119.8, 119.6,
118.9, 116.9, 115.5, 114.8, 63.6, 63.2, 57.5, 57.4, 14.3, 13.4.
Synlett 2012, 23, 877–880
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