Abstract
Recent advances in the preparation of β-lactams by ketene-imine [2+2] cycloadditions are described. Types of ketenes noted include those generated by thermal and photochemical means, with examples of stable and isolable ketenes, as well as reactive intermediates, sometimes observable by spectroscopic methods. Preparations of bis(β-lactams) by such processes are also described.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Staudinger H (1907) Zur Kenntniss der Ketene. Chem Ber 40:51–123. doi:10.1002/jlac.19073560106
Staudinger H (1905) Ketene, eine neue Körperklasse. Chem Ber 38:1735–1739. doi:10.1002/cber.19050380283
Tidwell TT (2005) The first century of ketenes (1905–2005): the birth of a versatile family of reactive intermediates. Angew Chem Int Ed 44:5778–5785. doi:10.1002/anie.200500098
Seeman JI (2015) Woodward-Hoffmann’s stereochemistry of electrocyclic reactions: from day 1 to the JACS receipt date (May 5, 1964 to November 30, 1964). J Org Chem 80:11632–11671. doi:10.1021/acs.joc.5b01792
Wikipedia, accessed April 1, 2016
Singh GS, Sudheesh S (2014) Advances in synthesis of monocyclic β-lactams. ARKIVOC 337–385. doi:10.3998/ark.5550190.0015.100
Banik BK (2014) Novel synthesis of β-lactams and their biological evaluation. J Indian Chem Soc 91:1837–1860
Pracejus H (1960) Organische Katalysatoren, LXI. Asymmetrische Synthesen mit Ketenen, I. Alkaloid-katalysierte asymmetrische Synthesen von α-Phenyl-propionsäureestern. Liebigs Ann Chem 634:9–22. doi:10.1002/jlac.19606340103
Wynberg H, Staring EG (1982) Asymmetric synthesis of (S)- and (R)-malic acid from ketene and chloral. J Am Chem Soc 104:166–168. doi:10.1021/ja00365a030
Magriotis PA (2014) Progress in asymmetric organocatalytic synthesis of β-lactams. Eur J Org Chem 2647–2657. doi:10.1002/ejoc.201301720
Tuba R (2013) Synthesis of β-lactams by transition metal promoted Staudinger reactions: alternative synthetic approaches from transition metal enhanced organocatalysis to in situ, highly reactive intermediate synthesis and catalytic tandem reactions. Org Biomol Chem 11:5976–5988. doi:10.1039/c3ob41048j
Hans M, Wouters J, Demonceau A, Delaude L (2013) Mechanistic insight into the Staudinger reaction catalyzed by N-heterocyclic carbenes. Chem Eur J 19:9668–9676. doi:10.1002/chem.201204428
Zhang H-M, Gao Z-H, Ye S (2014) Bifunctional N‐heterocyclic carbene-catalyzed highly enantioselective synthesis of spirocyclic oxindolo-β-lactams. Org Lett 16:3079–3081. doi:10.1021/ol501205v
Wang Y, Wei D, Li Z, Zhu Y, Tang M (2014) DFT Study on the mechanisms and diastereoselectivities of lewis acid-promoted ketene–alkene [2+2] cycloadditions: what is the role of lewis acid in the ketene and C=X (X=O, CH2, and NH) [2+2] cycloaddition reactions? J Phys Chem A 118:4288–4300. doi:10.1021/jp500358m
Zarei M (2013) A convenient synthesis of 2-azetidinones via 2-fluoro-1-methylpyridinium p-toluenesulfonate. Monat Chem 144:1021–1025. doi: 10.1007/s00706-012-0918-y
Zarei M (2014) An efficient and green method for the synthesis of 2-azetidinones mediated by propylphosphonic anhydride (T3). Monat Chem 145:1495–1499. doi:10.1007/s00706-014-1217-6
Mandler MD, Truong PM, Zavalij PY, Doyle MP (2014) Catalytic conversion of diazocarbonyl compounds to imines: applications to the synthesis of tetrahydropyrimidines and β-lactams. Org Lett 16:740–743. doi:10.1021/ol403427s
Feroci M (2011) Investigation of the role of electrogenerated N-heterocyclic carbene in the Staudinger synthesis in ionic liquid. Int J Org Chem 1:191–201. doi:10.4236/ijoc.2011.14028
Toyoda Y, Ninomiya M, Ebihara M, Koketsu M (2013) The staudinger reaction with 2-imino-1,3-thiaselenanes toward the synthesis of C4 spiro-β-lactams. Org Biomol Chem 11:2652–2659. doi:10.1039/c3ob00073g
Feroci M, Chiarotto I, Orsini M, Inesi A (2010) Electrogenerated NHC as an organocatalyst in the Staudinger reaction. Chem Commun 46:4121–4123. doi:10.1039/c002325f
Okano T (2013) Heterocyclic synthesis via catalysis of N-heterocyclic carbenes: very classical and very modern chemical species. Heterocyclic Commun 19:311–326. doi:10.1515/hc-2013-0075
Hafner A, Ley SV (2015) Generation of reactive ketenes under flow conditions through zinc-mediated dehalogenation. Synlett 1470–1474. doi:10.1055/s-0034-1380679
Hosseinkhani B, Islami MR, Hosseinkhani S (2015) Highly stereoselective synthesis of isoindole derivatives containing an azetidinone ring. Synlett 2277–2279. doi:10.1055/s-0035-15660066
Stoll T, Alker A, Kolczewski S, Menzi A, Revil-Baudard V (2015) New short access to pyrrolo[2,3-c]pyridazin-6-ones via b-spirolactams. Tetrahedron Lett 56:772–774. doi:10.1016/j.tetlet.2014.12.017
Karlsson S, Bergman R, Löfberg C, Moore P, Ponten F, Tholander J, Sörensen H (2015) Development of a large-scale route to an MCH1 receptor antagonist: investigation of a Staudinger ketene-imine cycloaddition in batch and flow mode. Org Proc Res Dev 19:2067–2074. doi:10.1021/acs.oprd.5b00319
de Bruin B, Tang Z, Mandal S, Paul ND, Lutz M, Li P, van der Vlugt JI (2015) Rhodium catalysed conversion of carbenes into ketenes and ketene imines using PNN pincer complexes. Org Chem Front 2:1561–1577. doi:0.1039/c5qo00287g
Zhang H-M, Gao Z-H, Ye S (2014) Bifunctional N-heterocyclic carbene-catalyzed highly enantioselective synthesis of spirocyclic oxindolo-β-lactams. Org Lett 16:3079–3081. doi:10.1021/ol501205v
Hans M, Wouters J, Demonceau A, Delaude L (2015) Probing the diastereoselectivity of Staudinger reactions catalyzed by N-heterocyclic carbenes. Chem Eur J 21:10870–10877. doi:10.1002/chem.201501060
Santoro S, Liao R-Z, Marcelli T, Hammar P, Himo F (2015) Theoretical study of mechanism and stereoselectivity of catalytic kinugasa reaction. J Org Chem 80:2649–2660. doi:10.1021/jo502838p
Zarei M (2014) A straightforward approach to 2-azetidinones from imines and carboxylic acids using dimethyl sulfoxide and acetic anhydride. Tetrahedron Lett 55:5354–5357. doi:10.1016/j.tetlet.2014.07.089
Jarrahpour A, Heiran R (2014) Synthesis of new nanocopolymer containing β-lactams. J Iran Chem Soc 11:75–83. doi:10.1007/s13738-013-0277-6
Jarrahpour A, Ebrahimi E, Sinou V, Latour C, Brunel JM (2014) Diastereoselective synthesis of potent antimalarial cis-β-lactam agents through a [2+2] cycloaddition of chiral imines with a chiral ketene. Eur J Med Chem 87:364–371. doi:10.1016/j.ejmech.2014.09.077
Jarrahpour A, Nazari M (2015) Synthesis of some new polycyclic aromatic monocyclic β-lactams. Iran J Sci Tech, Trans A: Science 39:259–265. url:http://ijsts.shirazu.ac.ir
Domingo LR, Sáez JA (2014) Understanding the selectivity in the formation of β-lactams vs. β-lactams in the Staudinger reactions of chloro-cyan-ketene with unsaturated imines. A DFT study. RSC Adv. 4:58559–58566. doi:10.1039/C4RA10291F
Zheng R, Wang Y, Zhang L (2015) Ruthenium-catalyzed rearrangement of propargyl sulfoxides: formation of a,β-unsaturated thioesters. Tetrahedron Lett 56:3144–3146. doi:10.1016/j.tetlet.2014.11.138
Huang Z, Wang C, Tokunaga E, Shibata N (2015) Stereoselective synthesis of β‐lactam-triflones under catalyst-free conditions. Org Lett 17:5610–5613. doi:10.1021/acs.orglett.5b02827
Jarrahpour A, Shirvani P, Sinou V, Latour C, Brunel (2016) Synthesis and biological evaluation of some new β-lactam-triazole hybrids. J M Med Chem Res 25:149–162. doi:10.1007/s00044-015-1474-x
Behzadi M, Saidi K, Islami MR, Khabazzadeh H (2016) Experimental and theoretical investigation of benzyl-N-pyrrolylketene, one- step procedure for preparing of new β-lactams by [2+2] cycloaddition reaction. J Chem Sci 128:111–117. doi:10.1007/s12039-015-1007-7
Mortazavi ZFA, Islami MR, Khaleghi M (2015) Highly stereoselective synthesis of saccharin-substituted β-lactams via in situ generation of a heterosubstituted ketene and a zwitterionic intermediate as potential antibacterial agents. Org Lett 17:3034–3037. doi:10.1021/acs.orglett.5b01309
Hosseinkhani B, Islami MR, Hosseinkhani S (2015) Highly stereoselective synthesis of isoindole derivatives containing an azetidinone ring. Synlett 2277–2279. doi:10.1055/s-0035-1560066
Sharma P, Ahuja M, Kumar A, Sahu V (2015) Contribution of reactivity indexes in the formation of β-lactams through [2+2] cycloaddition between substituted ketenes and imines. Chem Phys Lett 628:85–90. doi:10.1016/j.cplett.2015.04.005
Tang Z, Mandal S, Paul ND, Lutz M, Li P, van der Vlugt JI, de Bruin B (2015) Rhodium catalysed conversion of carbenes into ketenes and ketene imines using PNN pincer complexes. Org Chem Front 1561–1577. doi:10.1039/c5qo00287g
Berber N, Arslan M, Bilen C, Sackes Z, Gencer N, Arslan O (2015) Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors. Russ J Bioorg Chem 41:414–420. doi:10.1134/S1068162015040111
Jarrahpour A, Shirvani P, Sinou V, Latour C, Brunel JM (2016) Synthesis and biological evaluation of some new β-lactam-triazole hybrids. Med Chem Res 25:149–162. doi:10.1007/s00044-015-1474-x
Jarrahpour A, Nazari M (2015) Synthesis of some new polycyclic aromatic monocyclic β-lactams. Iran J Sci Tech, Trans A Sci 39:259–265
Jarrahpour A, Aye M, Sinou V, Latour C, Brunel JM (2015) Synthesis of some new monocyclic β-lactams as antimalarial agents. J Iran Chem Soc 12:2083–2092. doi:10.1007/s13738-015-0685-x
Li X, Jin X, Xu J (2015) Annuloselectivity in Reactions Of Diacyl Dichlorides And Imines: Combined Experimental And Theoretical Studies. J Org Chem 80:6976–6985. doi:10.1021/acs.joc.5b00573
Arumugam N, Almansour AI, Kumar RS, Rajesh R, Periyasami G, Raghunathan R (2014) Synthesis and antimicrobial evaluation of novel bis-β-lactam grafted macrocycles. Med Chem 10:730–737. doi:10.2174/1573406410666140226115258
Bains D, Kumar Y, Singh P, Bhargava G (2016) [2+2] Cycloaddition reactions of butadienyl ketene with 1,4-diazabuta-1,3-dienes: synthesis of functionalized butadienyl-4-iminomethyl-azetidin-2-ones and Butenylidene-butadienyl-[2,2′-biazetidine]-4,4′-diones. J Het Chem in press. still not final as of May 1, 2016, 53:1665–1669. doi:10.1002/jhet.2465
Jetti V, Chidurala P, Pagadala R, Meshram JS, Ramakrishna C (2014) Ultrasound-assisted one-pot synthesis of bis-azetidinones in the presence of zeolite. J Het Chem E183–E188 doi:10.1002/jhet.1922pdfJHC2014E183
Tidwell TT (2013) Preparation of bis-β-Lactams by ketene-imine cycloaddition. Top Heterocycl Chem 30:111–146. doi:10.1007/7081_2012_89
Arumugam N, Almansour AI, Kumar RS, Rajesh R, Periyasami G, Raghunathan R (2014) Synthesis and antimicrobial evaluation of novel bis-β-lactam grafted macrocycles. Med Chem 10:730–737. doi:10.2174/1573406410666140226115258
Ibrahim YA, Al-Awadi NA, Al-Azemi TF, Abraham SJE (2013) Sequential staudinger ketene–imine cycloaddition, RCM approach to polycyclic macrocyclic bisazetidinones. RSC Adv 3:6408–6416. doi:10.1039/c3ra40649k
Qi H, Li X, Xu J (2011) Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: experimental investigation and theoretical rationalization. Org Biomol Chem 9:2702–2714. doi:10.1039/c0ob00783h
Zheng R, Wang Y, Zhang L (2015) Ruthenium-catalyzed rearrangement of propargyl sulfoxides: formation of a, b-unsaturated thioesters. Tetrahedron Lett 56:3144–3146. doi:10.1016/j.tetlet.2014.11.138
Liang Y, Jiao L, Zhang S, Yu Z-X, Xu J (2009) New insights into the torquoselectivity of the Staudinger REACTION. J Am Chem Soc 131:1542–1549. doi:10.1021/ja808046e
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer International Publishing AG
About this chapter
Cite this chapter
Tidwell, T.T. (2017). β-Lactams from Ketene-Imine Cycloadditions: An Update. In: Banik, B. (eds) Beta-Lactams. Springer, Cham. https://doi.org/10.1007/978-3-319-55621-5_4
Download citation
DOI: https://doi.org/10.1007/978-3-319-55621-5_4
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-55620-8
Online ISBN: 978-3-319-55621-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)