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358ꢀ ꢀM. Zarei and A. Jarrahpour: Synthesis of 2-azetidinones
[13] Palomo, C.; Oiarbide, M. β-Lactam Ring Opening: A Useful
Entry to Amino Acids and Relevant Nitrogen-Containing
Compounds. In Topics Heterocycl. Chem. Banik, B. K., Ed.
Springer-Verlag: Berlin, 2010; Vol. 22, pp 211–259.
[14] Suffness, M. Taxol Science and Applications; CRC Press: Boca
Raton, FL, 1995.
[33] Zarei, M. A facile and effective synthesis of 2-azetidinones via
phosphonitrilic chloride. Tetrahedron 2013, 69, 6620–6626.
1568–1570.
[35] Jarrahpour, A.; Zarei, M. The Vilsmeier reagent: a useful and
versatile reagent for the synthesis of 2-azetidinones. Tetrahe-
dron 2009, 65, 2927–2934.
[15] Li, W.; Liu, C.; Zhang, H.; Ye, K.; Zhang, G.; Zhang, W.; Duan, Z.;
You, S.; Lei, A. Palladium-catalyzed oxidative carbonylation of
N-allylamines for the synthesis of β-lactams. Angew. Chem. Int. [36] Nahmany, M.; Melman, A. Simple approach to β-lactam deriva-
Ed. 2014, 53, 2443–2446.
tives from N-acylimidazoles. J. Org. Chem. 2006, 71, 5804–
5806.
[16] Darvishi, A.; Zarei, M.; Akhgar, M. R. A simple and highly efficient
procedure for one-pot synthesis of 2-azetidinones using 3,5-dini-
trobenzoyl chloride. Lett. Org. Chem. 2013, 10, 645–650.
[17] Alcaide, B.; Almendros, P. Four-Membered Ring Systems. In
Progress in Heterocyclic Chemistry. Gribble, G. W., Joule, J. A.,
Eds. Elsevier: Oxford, UK, 2011; Vol. 22, pp 85–107.
[18] Aguilar H.; Banik, B. K. Stereoselectivity of 3,3-disubstituted
β-lactam formation via Staudinger reaction. Heterocycl. Com-
mun. 2009, 15, 365–368.
[37] Jarrahpour, A.; Zarei, M. Synthesis of novel N-(4-ethoxyphenyl)
azetidin-2-ones and their oxidative N-deprotection by ceric
ammonium nitrate. Molecules 2007, 12, 2364–2379.
[38] Zarei, M. A convenient synthesis of 2-azetidinones via 2-fluoro-
1-methylpyridinium p-toluenesulfonate. Monatsh. Chem. 2013,
144, 1021–1025.
2007, 48, 8712–8714.
[19] Fu, N.; Tidwell, T. T. Preparation of β-lactams by [2+2] cycloaddi-
[20] Georg, G. I. The Organic Chemistry of β-Lactams; Verlag Che-
mie: New York, 1993.
ride. J. Chem. Res. 2013, 37, 25–27.
[41] Matsui, S.; Hashimoto, Y.; Saigo, K. Application of erythro-
2-amino-1,2-diphenylethanol as a highly efficient chiral auxil-
iary. Highly stereoselective Staudinger-type β-lactam synthesis
using a 2-chloro-1-methylpyridinium salt as the dehydrating
agent. Synthesis 1998, 1161–1166.
Liebigs Ann. Chem. 1907, 356, 51–123.
[22] Zarei, M. An efficient and green method for the synthesis of
2-azetidinones mediated by propylphosphonic anhydride
(T3P). Monatsh. Chem. 2014, 145, 1495–1499.
[23] Zarei, M.; Karimi-Jaberi, Z.; Movahedi, A. Synthesis of
zole. Synth. Commun. 2013, 43, 728–734.
[24] Jarrahpour, A.; Motamedifar, M.; Zarei, M.; Mimouni, M.
Synthesis of new N-sulfonyl monocyclic β-lactams and the
investigation of their antibacterial activities. Phosphorus
Sulfur Silicon 2010, 185, 287–297.
846–850.
[26] Jarrahpour, A.; Fadavi, A.; Zarei, M. Synthesis of structurally
diverse 2-azetidinones via Staudinger reaction on a solid sup-
port. Bull. Chem. Soc. Jpn. 2011, 84, 320–327.
[42] Bandyopadhyay, D.; Xavier, M.; Banik, B. K. Highly stereose-
lective β-lactam synthesis via the Staudinger reaction using
polyaromatic imines. Heterocycl. Commun. 2009, 15, 229–232.
[43] Palomo, C.; Aizpurua, J. M.; Urchegui, R.; Iturburu, M.; de
Retana, A. O.; Cuevas, C. A convenient method for β-lactam
formation from β-amino acids using phenyl phosphorodichlori-
date reagent. J. Org. Chem. 1991, 56, 2244–2247.
2013, 15, 258–261.
[45] Jarrahpour, A.; Ebrahimi, E.; Khalifeh, K.; Sharghi, H.;
Sahraei, M.; Sinou, V.; Latour, C.; Brunel, J. M. Synthesis
of novel b-lactams bearing an anthraquinone moiety, and
evaluation of their antimalarial activities. Tetrahedron 2012,
68, 4740–4744.
[27] Keri, R. S.; Hosamani, K. M.; Shingalapur, R. V.; Reddy, H. R. S.
2-Azetidinone derivatives: design, synthesis, in vitro anti-
microbial, cytotoxic activities and DNA cleavage study. Eur. J.
Med. Chem. 2009, 44, 5123–5130.
[28] Zarei, M.; Jarrahpour, A. A mild and efficient route to 2-azetidi-
nones using the cyanuric chloride-DMF complex. Synlett 2001,
22, 2572–2576.
[46] Zarei, M.; Mohamadzadeh, M. 3-Thiolated 2-azetidinones:
synthesis and in vitro antibacterial and antifungal activities.
Tetrahedron 2011, 67, 5832–5840.
3041–3044.
[29] Jarrahpour, A.; Zarei, M. Synthesis of novel N-sulfonyl mono-
cyclic β-lactams as potential antibacterial agents. Molecules
2006, 11, 49–58.
[49] Zarei, M. One-pot sequence synthesis of azetidin-2-one using
diethyl chlorophosphate. J. Chem. Res. 2012, 36, 118–120.
[50] Kanwar, S.; Sharma, S. D. Use of 2,2′-dibenzothiazolyl
disulfide-triphenylphosphine and Lawesson’s reagent in the
cyclization of β-amino acids Bull. Chem. Soc. Jpn. 2006, 79,
1748–1752.
[51] Bernardi, L.; Bonini, B. F.; Comes-Franchini, M.; Dessole, C.;
Fochi, M.; Ricci, A. One-pot synthesis of novel enantiomerically
pure and racemic 4-ferrocenyl-β-lactams and their reactivity in
acidic media. Eur. J. Org. Chem. 2005, 3326–3333.
[30] Tidwell, T. T. Ketenes II; John Wiley & Sons: Hoboken, NJ, 2006,
pp 55–192.
[31] Khadsan, R. E.; Kadu, M. V. Synthesis and biological
evaluation of some novel N-substitutedphenyl-4-(3′,4′-
methylenedioxyphenyl)-3-chloro-2-azetidinone derivatives.
Heterocycl. Commun. 2005, 11, 455–458.
[32] Zarei, M. A straightforward approach to 2-azetidinones from
imines and carboxylic acids using dimethyl sulfoxide and
acetic anhydride. Tetrahedron Lett. 2014, 55, 5354–5357.
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