6
Tetrahedron
4.17. Se-butyl benzoselenoate (3m)
128.8, 123.7. Anal. Calcd. For C13H8Cl2OSe: C, 47.31; H, 2.44%;
Found: C, 47.26; H, 2.37%.
Yellow oil, Yield: 61%, 139 mg; 1H NMR (CDCl3, 400 MHz):
4.26. N-benzylbenzamide (4a) [17]
δ 7.592-7.90 (m, 2H), 7.60-7.56 (m, 1H), 7.47-7.43 (m, 2H), 3.11
(t, J = 14.8 Hz, 2H), 1.76-1.70 (m, 2H), 1.48-1.43 (m, 2H), 0.95
(t, J = 16 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 195.2, 139.4,
133.6, 128.9, 127.3, 31.7, 29.2, 22.8, 13.8. Anal. Calcd. For
C11H14OSe: C, 54.78; H, 5.85%; Found: C, 54.85; H, 5.94%.
1
White solid, mp. 105-107 °C, Yield: 77%, 162 mg; H NMR
(CDCl3, 400 MHz): δ 7.81-7.79 (m, 2H), 7.51-7.27 (m, 8H), 6.58
(s, 1H), 4.64 (d, J = 5.6 Hz, 2H); 13C NMR (CDCl3, 100 MHz): δ
167.5, 138.4, 134.5, 131.6, 128.8, 128.7, 128.0, 127.6, 127.1.
4.18. Se-phenyl 3-methylbenzoselenoate (3o) [10]
4.27. N-(4-methoxybenzyl)benzamide (4b) [17]
Yellow oil, Yield: 78%, 214 mg; 1H NMR (CDCl3, 400 MHz):
δ 7.58-7.56 (m, 2H), 7.44-7.41 (m, 2H), 7.25-7.17 (m, 5H), 2.26
(s, 3H); 13C NMR (CDCl3, 100 MHz): δ 193.5, 139.0, 138.8,
136.5, 134.8, 129.5, 129.1, 128.9, 127.9, 126.1, 124.7, 21.4.
1
White solid, mp. 94-96 °C, Yield: 79%, 190 mg; H NMR
(CDCl3, 400 MHz): δ 7.79-7.77 (m, 2H), 7.45-7.37 (m, 3H), 7.28-
7.26 (m, 2H), 6.86-6.83 (m, 2H), 6.64 (s, 1H), 4.55 (d, J = 5.2
Hz, 2H), 3.76 (s, 1H); 13C NMR (CDCl3, 100 MHz): δ 167.3,
159.6, 134.5, 131.5, 130.5, 129.4, 128.6, 127.1, 114.1, 55.4, 43.6.
4.19. Se-phenyl 4-methylbenzoselenoate (3p) [14b]
1
White solid; mp. 95-97 °C; Yield: 81%, 222 mg; H NMR
Acknowledgments
(CDCl3, 400 MHz): δ 7.85-7.83 (m, 2H), 7.61-7.59 (m, 2H), 7.43-
7.42 (m, 3H), 7.32-7.27 (m, 2H), 2.42 (s, 3H); 13C NMR (CDCl3,
100 MHz): δ 192.9, 145.0, 136.2, 136.2, 129.7, 129.5, 129.1,
127.6, 126.1, 21.9.
A. Majee acknowledges financial support from the DST-RSF
Major Research Project (Ref. No. INT/RUS/RSF/P-08). S. Santra
is thankful to the Russian Science Foundation – Russia (Ref. #
18-73-00301) for funding. We are thankful to the DST-FIST and
UGC-SAP program.
4.20. Se-phenyl 4-fluorobenzoselenoate (3q)
1
Yellow gummy mass; Yield: 79%, 220 mg; H NMR (CDCl3,
400 MHz): δ 7.98-7.95 (m, 2H), 7.61-7.58 (m, 2H), 7.45-7.41 (m,
References and notes
3H), 7.19-7.15 (m, 2H); 13C NMR (CDCl3, 100 MHz): δ 191.9,
1
3
166.3, (d, JC-F = 254 Hz), 136.4, 135.1 (d, JC-F = 2 Hz), 130.1,
1. (a) G. Mugesh, W. W. Du Mont, H. Sies, Chem. Rev. 101 (2001)
2125–2179; (b) H. Xu, W. Cao, X. Zhang, Acc. Chem. Res. 46
(2013) 1647–1658; (c) S. Santoro, J. B. Azeredo, V. Nascimento,
L. Sancineto, A. L. Braga, C. Santi, RSC Adv. 4 (2014), 31521–
31535; (d) D. Tanini, C. Tiberi, C. Gellini, P. R. Salvi, A.
Capperucci, Adv. Synth. Catal. 360 (2018) 3367–3375.
2. (a) C. W. Nogueira, G. Zeni, J. B. T. Rocha, Chem. Rev. 104
(2004) 6255–6286; (b) B. K. Sarma , G. Mugesh, Org. Biomol.
Chem. 6 (2008) 965–974; (c) E. Domínguez-Álvarez, M. Gajdács,
G. Spengler, J. A. Palop, M. A. Marć, K. Kieć-Kononowicz, L.
Amaral, J. Molnár, C. Jacob, J. Handzlik, C. Sanmartín,
4
2
(d, JC-F = 9 Hz), 129.5, 129.3, 116.3 (d, JC-F = 22 Hz). Anal.
Calcd. For C13H9FOSe: C, 55.93; H, 3.25%; Found: C, 55.86; H,
3.35%;
4.21. Se-phenyl 3-chlorobenzoselenoate (3r)
1
White solid; mp. 73-75 °C; Yield: 77%, 227 mg; H NMR
(CDCl3, 400 MHz): δ 7.71-7.70 (m, 1H), 7.64-7.62 (m, 1H), 7.42-
7.38 (m, 3H), 7.27-7.22 (m, 4H); 13C NMR (CDCl3, 100 MHz): δ
192.5, 140.2, 136.3, 135.4, 133.8, 130.3, 129.6, 129.4, 127.3,
125.6, 125.5. Anal. Calcd. For C13H9ClOSe: C, 52.82; H, 3.07%;
Found: C, 52.94; H, 3.16%.
Bioorganic Med. Chem. Lett. 26 (2016) 2821–2824; (d) D. Plano,
M. Font, J. A. Palop, E. Moreno, C. Sanmartín, I. Encío, Arch.
Pharm. (Weinheim). 343 (2010) 680–691; (e) M. Gajdács, G.
Spengler, C. Sanmartín, M. A. Marć, J. Handzlik, E. Domínguez-
Álvarez, Bioorganic Med. Chem. Lett. 27 (2017) 797–802; (f) G.
Mugesh, H. B. Singh, Chem. Soc. Rev. 29 (2000) 347–357; (g) H.
D. Salles, E. J. Lenardão, L. Savegnago, D. Alves, P. H.
Schneider, A. M. Casaril, D. M. Martinez, M. Castro, F. N.
Victoria, Chem. Biol. Interact. 205 (2013) 100–107; (h) V.
Gandin, P. Khalkar, J. Braude, A. P. Fernandes, Free Radic. Biol.
Med. 127 (2018) 80–97; (i) A. Fuentes-Aguilar, L. L. Romero-
Hernández, A. Arenas-González, P. Merino-Montiel, S. Montiel-
Smith, S. Meza-Reyes, J. L. Vega-Báez, G. B. Plata, J. M. Padrón,
Ó. López, J. G. Fernández-Bolaños, Org. Biomol. Chem. 15
(2017) 5041–5054; (j) P. Khalkar, N. Díaz-Argelich, J. A. Palop,
C. Sanmartín, A. P. Fernandes, Int. J. Mol. Sci. 19 (2018) 2849;
(k) K. M. Peters, B. A. Carlson, V. N. Gladyshev, P. A. Tsuji,
Free Radic. Biol. Med. 127 (2018) 14–25; (l) J. A. Palop, C.
Sanmartín, A. P. Fernandes, N. Díaz-Argelich, I. Encío, D. Plano,
Molecules 22 (2017) 1288; (m) C. Prior, E. Domínguez-Álvarez,
D. Plano, J. A. Palop, A. Calvo, M. Font, C. Jacob, C. Sanmartín,
Eur. J. Med. Chem. 73 (2013) 153–166.
4.22. Se-phenyl 4-chlorobenzoselenoate (3s) [14b]
1
White solid; mp. 82-84 °C; Yield: 80%, 236 mg; H NMR
(CDCl3, 400 MHz): δ 7.88-7.86 (m, 2H), 7.60-7.57 (m, 2H), 7.48-
7.42 (m, 5H); 13C NMR (CDCl3, 100 MHz): δ 192.4, 140.4,
137.1, 136.4, 129.6, 129.4 (2C), 128.8, 125.7.
4.23. Se-phenyl 4-bromobenzoselenoate (3t) [14b]
1
White solid; mp. 96-98 °C; Yield: 78%, 265 mg; H NMR
(CDCl3, 400 MHz): δ 7.80-7.78 (m, 2H), 7.64-7.62 (m, 2H), 7.60-
7.57 (m, 2H), 7.45-7.41 (m, 3H); 13C NMR (CDCl3, 100 MHz): δ
192.6, 137.5, 136.4, 132.4, 129.6, 129.4, 129.1, 128.8, 125.6.
4.24. Se-(4-chlorophenyl)-4-methylbenzoselenoate (3u)
1
White gummy mass; Yield: 75%, 231 mg; H NMR (CDCl3,
3. (a) M. Inoue, S. Yamashita, Y. Ishihara, M. Hirama, Org. Lett. 8
(2006) 5805–5808; (b) Priv. Doz. G. Heppke, K. Praefcke, H.
Simon, Angew. Chem. Int. Ed. Engl. 16 (1977) 318-319.
4. (a) D. L. Boger , R. J. Mathvink, J. Org. Chem. 54 (1989) 1777–
1779; (b) D. L. Boger, R. J. Mathvink, J. Org. Chem. 57 (1992)
1429–1443; (c) A. P. Kozikowski, A. Ames, Tetrahedron 41
(1985) 4821–4834; (d) A. F. Sviridov, M. S. Ermolenko, D. V.
Yashunsky, N. K. Kochetkov, Tetrahedron Lett. 24 (1983) 4355-
4358; (e) J. Quirante, X. Vila, C. Escolano, J. Bonjoch, J. Org.
Chem. 67 (2002) 2323–2328.
400 MHz): δ 7.82-7.80 (m, 2H), 7.53-7.49 (m, 2H), 7.40-7.37 (m,
2H), 7.30-7.27 (m, 2H), 2.42 (s, 3H); 13C NMR (CDCl3, 100
MHz): δ 192.3, 145.3, 137.8, 135.8, 135.6, 129.8, 129.7, 127.6,
124.2, 21.9. Anal. Calcd. For C14H11ClOSe: C, 54.30; H, 3.58%;
Found: C, 54.39; H, 3.50%.
4.25. Se-(4-chlorophenyl)-4-chlorobenzoselenoate (3v)
1
White gummy mass; Yield: 72%, 237 mg; H NMR (CDCl3,
5. (a) G. E. Keck, M. C. Grier, Synlett (1999) 1657–1659; (b) C.
Chen, D. Crich, A. Papadatos, J. Am. Chem. Soc. 114 (1992)
8313-8314; (c) Grélaud, J. Lusseau, S. Massip, Y. Landais, Adv.
Synth. Catal. 359 (2017) 2434.
400 MHz): δ 7.78-7.75 (m, 1H), 7.49-7.46 (m, 2H), 7.43-7.37 (m,
2H), 7.32-7.30 (m, 1H), 7.29-7.26 (m, 2H); 13C NMR (CDCl3,
100 MHz): δ 192.1, 145.2, 137.7, 135.9, 129.8, 129.5, 129.2,