M. Zarei
Vol 000
[7] (a)Palomo, C.; Oiarbide, M. In Topics in Heterocyclic
C33H25NO4: C, 79.34; H, 5.04; N, 2.80. Found: C, 79.27;
H, 5.13; N, 2.83.
2-(4-Chlorophenyl)-1-(4-methoxynaphthalen-1-yl)spiro[azetidine-
Chemistry; Banik, B. K., Ed.; Springer-Verlag; Berlin; 2010; Vol. 22,
pp 211–259; (b) Alcaide, B.; Almendros, P. Chem Rec 2011, 11, 311; (c)
Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem Rev 2007, 107, 4437.
[8] Hodge, M.; Chen, O.-H.; Bane, S.; Sharma, S.; Loew, M.;
Banerjee, A.; Alcaraz, A. A.; Snyder, J. P.; Kingston, D. G. I. Bioorg
Med Chem Lett 2009, 19, 2884.
3,9′-xanthen]-4-one (8d). White solid. mp: 161–163°C IR
1
(KBr) cmꢀ1: 1756 (CO, β-lactam); H-NMR (CDCl3) δ
3.61 (OMe, s, 3H), 5.42 (H-4, s, 1H), 6.86–7.62 (ArH,
m, 16H); 13C-NMR (CDCl3) δ 56.0 (OMe), 66.8 (C-4),
73.7 (C-3), 116.5–152.1 (aromatic carbons), 164.1 (CO,
β-lactam); Anal. Calcd for C32H22ClNO3: C, 76.26; H,
4.40; N, 2.78. Found: C, 76.18; H, 4.49; N, 2.74.
[9] For review see: (a) Alcaide, B.; Almendros, P. Progress in
Heterocyclic Chemistry 2011, 22, 85–107; (b) Aranda, M. T.; Perez-Faginas,
P.; Gonzalez-Muniz, R. Curr Org Synth 2009, 6, 325; (c) Fu, N.; Tidwell, T.
T. Tetrahedron 2008, 64, 10465; (d) Xu, J. Tetrahedron 2012, 68, 10696; (e)
Kamath, A.; Ojima, I. Tetrahedron 2012, 68, 10640.
[10] Staudinger, H. Liebigs Ann Chem 1907, 356, 51.
[11] (a) Fodor, L.; Csomos, P.; Holczbauer, T.; Kalman, A.;
Csampai, A.; Sohar, P. Tetrahedron Lett 2011, 52, 224; (b) Zarei, M.;
Karimi-Jaberi, Z.; Movahedi, A. Synth Commun 2013, 43, 728;
(c) Keri, R. S.; Hosamani, K. M.; Shingalapur, R. V.; Reddy, H. R. S.
Eur J Med Chem 2009, 44, 5123; (d) Zarei, M.; Jarrahpour, A. Synlett
2011 2572; (e) Zarei, M.; Mohamadzadeh, M. Tetrahedron 2011, 67,
5832; (f) Jarrahpour, A.; Nazari, M. Iran J Sci Technol A 2015, 39, 259.
[12] (a) Tidwell, T. T. Ketenes II; John Wiley & Sons: New Jersey,
2006, pp 55–192; (b) Jarrahpour, A.; Zarei, M. Molecules 2006, 11, 49;
(c) Pagadala, R.; Meshram, J. S.; Chopde, H. N.; Jetti, V.; Udayini, V. J.
Heterocyclic Chem 2011, 48, 1067.
1-(Benzo[d]thiazol-2-yl)-2-(4-methoxyphenyl)spiro[azetidine-
3,9′-xanthen]-4-one (8e).
Pale yellowish solid. mp:
151–153°C IR (KBr) cmꢀ1: 1637 (C¼N), 1755 (CO,
1
β-lactam); H-NMR (CDCl3) δ 3.68 (OMe, s, 3H), 5.29
(H-4, s, 1H), 6.82–7.99 (ArH, m, 16H). 13C-NMR
(CDCl3)
δ 56.2 (OMe), 62.2 (C-4), 71.8 (C-3),
108.9–154.9 (aromatic carbons), 161.8 (C¼N), 166.0
(CO, β-lactam); Anal. Calcd for C29H20N2O3S: C, 73.09;
H, 4.23; N, 5.88. Found: C, 73.17; H, 4.33; N, 5.83.
1-(Benzo[d]thiazol-2-yl)-2-(4-chlorophenyl)spiro[azetidine-
[13] (a) Unsworth, W. P.; Coulthard, G.; Kitsiou, C.; Taylor, R. J.
K. J Org Chem 2014, 79, 1368; (b) Zarei, M. J Chem Res 2012, 36,
118; (c) Jarrahpour, A.; Ebrahimi, E.; Sinou, V.; Latour, C.; Brunel, J.
M. Eur J Med Chem 2014, 87, 364.
3,9′-xanthen]-4-one (8f).
Pale yellowish solid. mp:
155–157°C IR (KBr) cmꢀ1: 1632 (C¼N), 1744 (CO,
[14] (a) Smith, S. R.; Douglas, J.; Prevet, H.; Shapland, P.;
Slawin, A. M. Z.; Smith, A. D. J Org Chem 2014, 79, 1626; (b) Darvishi, A.;
Zarei, M.; Akhgar, M. R. Lett Org Chem 2013, 10, 645; (c) Jarrahpour, A.;
Zarei, M. Tetrahedron Lett 2009, 50, 1568; (d) Khademi Shiraz, A.;
Zarei, M. Monatsh Chem 2015, 146, 941; (e) Nahmany, M.; Melman, A.
J Org Chem 2006, 71, 5804; (f) Jarrahpour, A.; Zarei, M. Molecules
2007, 12, 2364; (g) Bose, A. K.; Kapur, J. C.; Sharma, S. D.;
Manhas, M. S. Tetrahedron Lett 1973 2319; (h) Jarrahpour, A.; Zarei, M.
Tetrahedron Lett 2007, 48, 8712; (i) Zarei, M. J Chem Res 2013, 37, 25;
(j) Zarei, M.; Jarrahpour, A. Heterocycl Commun 2014, 20, 355;
(k) Chopde, H. N.; Pagadala, R.; Meshram, J. S.; Jetti, V. JHeterocyclic
Chem 2010, 47, 1361; (l) Zarei, M. Monatsh Chem 2013, 144, 1021;
(m) Jarrahpour, A.; Motamedifar, M.; Zarei, M.; Mimouni, M. Phosphorus
Sulfur Silicon 2010, 185, 287; (n) Zarei, M. Lett Org Chem 2015, 12, 44;
(o) Coulthard, G.; Unsworth, W. P.; Taylor, R. J. K. Tetrahedron Lett
2015, 56, 3113; (p) Jarrahpour, A.; Ebrahimi, E.; Sinou, V.; Latour, C.;
Brunel, J. M. Eur J Med Chem 2014, 87, 364.
1
β-lactam); H-NMR δ 5.14 (H-4, s, 1H), 6.78–7.96 (ArH,
m, 16H); 13C-NMR δ 62.4 (C-4), 71.2 (C-3), 108.7–
154.2 (aromatic carbons), 161.5 (C¼N), 164.0 (CO,
β-lactam); Anal. Calcd for C28H17ClN2O2S: C, 69.92; H,
3.56; N, 5.82. Found: C, 70.01; H, 3.69; N, 5.87.
Acknowledgments. Thanks are due to the Iran National Science
Foundation (INSF-91059658) and Hormozgan University
Research Council for the financial support of this study
REFERENCES AND NOTES
[15] Zarei, M. Tetrahedron Lett 2014, 55, 5354.
[1] Tidwell, T. T. Synthesis 1990, 22, 857.
[2] Song, Y.; Shen, D.; Zhang, Q.; Chen, B.; Xu, G. Tetrahedron
Lett 2014, 55, 639.
[3] Petronijevic, Z.; Maluckov, B.; Smelcerovic, A. Tetrahedron
Lett 2013, 54, 3210.
[4] (a) Pérez-Ruiz, R.; Sáez, J. A.; Domingo, L. R.; Jiménez, M. C.;
Miranda, M. A. Org Biomol Chem 2012, 10, 7928; (b) Hwu, J. R.;
Ethiraj, S. K.; Hakimelahi, G. H. Mini-Rev Med Chem 2003, 3, 305.
[5] Earl, J.; Kirkpatrick, P. Nat Rev Drug Discov 2003, 2, 97.
[6] (a) Mehta, P. D.; Sengar, N. P. S.; Pathak, A. K. Eur J Med
Chem 2010, 45, 5541; (b) Arya, N.; Jagdale, A. Y.; Patil, T. A.;
Yeramwar, S. S.; Holikatti, S. S.; Dwivedi, J.; Shishoo, C. J.; Jain, K. S.
Eur J Med Chem 2014, 74, 619.
[16] Georg, G. I. The Organic Chemistry of β-Lactams; New York:
Verlag Chemie, 1993.
[17] Gutch, P. K.; Acharya, J. Heterocycl Commun 2007, 13, 393.
[18] (a) Wang, Y.; Liang, Y.; Jiao, L.; Du, D.-M.; Xu, J. J Org
Chem 2006, 71, 6983; (b) Jarrahpour, A.; Zarei, M. Tetrahedron 2010,
66, 5017; (c) Zarei, M. Bull Chem Soc Jpn 2012, 85, 360.
[19] (a) Zarei, M.; Jarrahpour, A.; Ebrahimi, E.; Aye, M.;
Torabi Badrabady, S. A. Tetrahedron 2012, 68, 5505; (b) Jarrahpour, A.;
Zarei, M. Phosphorus Sulfur Silicon 2009, 184, 1738; (c) Akkurt, M.; Karaca,
S.; Jarrahpour, A.; Zarei, M.; Büyükgünör, O. Acta Crystallogr Sect E 2008,
64, 924; (d) Matsui, S.; Hashimoto, Y.; Saigo, K. Synthesis 1998 1161; (e)
Jarrahpour, A.; Zarei, M. Tetrahedron 2009, 65, 2927; (f) Zarei, M.
Tetrahedron 2013, 69, 6620; (g) Zarei, M. Monatsh Chem 2014, 145, 1495.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet