Related Experiment Video
Updated: Jul 7, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of Novel cis-2-Azetidinones from imines and aclychloride using triethylamine
Handan Can Sakarya1, Aslı Ketrez2
1Department of Chemistry, Faculty of Arts and Science, Eskişehir Osmangazi University, 26480 Eskişehir. handansakarya26@gmail.com.
Abstract:
A novel series of cis-2-azetidinones 2(a-c ) was carried out by the cyclo addition reaction of imine 1(a-c ) and acyl chloride in dry dichloromethane at 0-5 oC using triphenylamine. The cyclo addition of the Schiff bases with chloroacetyl chloride resulted corresponding major product cis-2-azetidinone stereoisomers 2(a-c). The synthesized compounds were characterized by analytical and spectral (Infrared, 1H NMR, 13C NMR, and elemental analysis) data. Keywords: Benzothiazole, β-lactam, Schiff base, cis-2-azetidinone, Staudinger reaction Acknowledgements The authors would like to thank the Eskişehir Osmangazi University Scientific Research Projects Council for financial support (Project No: 2014/19A208). References • C. M. L. Delpiccolo, M. A. Fraga, E. G. Mata, J. Comb. Chem. 2003, 5, 208-210. DOI: 10.1021/cc020107d. • R. B. Pawar, V. V. Mulwad, Chem. Heterocycl. Compd. 2004, 40, 219-226. DOI: 10.1023/B:COHC.0000027896.38910.d1. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • G. S. Singh, B. J. Mmolotsi, Il Farmaco, 2005, 60, 727-730. DOI: 10.1016/j.farmac.2005.06.008. • C. D. Risi, G. P. Pollini, A. C. Veronese, V. Bertolasi, Tetrahedron Lett. 1999, 40, 6995-6998. DOI: 10.1016/S0040-4039(99)01421-5. • H. G. I. Georg: The Organic Chemistry of β-Lactams, Weinheim/VCH Publishers, New York, 1993, p. 295. DOI: 10.1002/ange.19941060738. • R. F. Abdulla, K. H. Fuhr, J. Med. Chem. 1975, 18, 625-627. DOI: 10.1021/jm00240a022. • W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. DOI: 10.1002/anie.198501801. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • H. Staudinger, Justus Liebigs Ann. Chem. 1907, 356, 51-123. DOI: 10.1002/jlac.19073560106. • A. K. Bose, M. Jayaraman, A. Okawa, S. S. Bari, E. W. Robb, M. S. Manhas, Tetrahedron Lett. 1996, 37, 6989-6992. DOI: 10.1016/0040-4039(96)01571-7. • A. K. Bose, B. K. Banik, M. S. Manhas, Tetrahedron Lett. 1995, 36, 213-216. DOI: 10.1016/0040-4039(94)02225-Z. • A. Arrieta, B. Lecea, F. P. Cossio, J. Org. Chem. 1998, 63, 5869-5876. DOI: 10.1021/jo9804745. • P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, G. Poni, C. A. Cabras, P. L. Colla, Bioorg. Med. Chem. 2003, 11, 4785-4789. DOI: 10.1016/S0968-0896(03)00493-0. • K. Mogilaiah, R. B. Rao, K. N. Reddy, Indian J. Chem. 1999, 38B, 818-822. • 16. I. Georg, V. T. G. I. Ravikumar, Ed. Verlag Chemie, 1993, 295- 368 New York, • L. Jiao, Y. Liang, J. Xu. J. Am. Chem. Soc. 2006, 128, 6060- 6069 • H. C. Sakarya, M. Yandımoğlu, Croat. Chem. Acta, 2018, 91, 533-541. DOI: 10.5562/cca3386. • D. A. Nelson, J. Org. Chem. 1972, 37, 1447-1449. DOI: 10.1021/jo00974a038. • K. D. Barrow, T. M. Spotswood, Tetrahedron Lett. 1965, 6, 3325-3335. DOI: 10.1016/S0040-4039(01)89203-0. • J. Decazes, J. L. Luche, H. B, Kagan, Tetrahedron Lett. 1970, 11, 3665-3668. DOI: 10.1016/S0040-4039(01)98556-9. • D. A. Nelson, Tetrahedron Lett. 1971, 12, 2543-2546. DOI: 10.1016/S0040-4039(01)96914-X.
More Related Videos
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...