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Journal articles on the topic 'Unsubstituted β-lactam'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Gallagher, Timothy, Sylvie Sanchez, John H. Bateson, and Peter J. O'Hanlon. "Thiocarbonyl-based 1,3-dipolarophiles for the synthesis of C(2)-unsubstituted penems." Pure and Applied Chemistry 77, no. 12 (2005): 2033–40. http://dx.doi.org/10.1351/pac200577122033.

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The azomethine ylid strategy for β-lactam synthesis, which involves the fragmentation of a β-lactam-based oxazolidinone to give a carboxylated azomethine ylid, has been extended to the C(2)-unsubstituted penem scaffold associated with C(6)-exoalkylidene penems. This involved the use of S-methyl dithioformate as a reactive 1,3-dipolarophile, which was most effectively employed by initial trapping with cyclopentadiene and subsequent regeneration of S-methyl dithioformate via a retro Diels-Alder reaction in the presence of the requisite oxazolidinone. This provided access to the penam scaffold, a

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2

Ram, Naresh Yadav, Banik Indrani та Krishna Banik Bimal. "Microwave-mediated synthesis of 3-unsubstituted β-lactams with aqueous trimethylborane". Journal of Indian Chemical Society Vol. 95, Nov 2018 (2018): 1381–84. https://doi.org/10.5281/zenodo.5652771.

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Department of Chemistry, Faculty of Engineering & Technology, Veer Bahadur Singh Purvanchal University, Jaunpur-222 003, Uttar Pradesh, India Department of Chemistry, University of Texas-Pan American,1201 W. University Dr., Edinburg, TX 78539, USA The University of Texas M. D. Anderson Cancer Center, Department of Molecular Pathology, 1515 Holcombe Blvd, Houston, TX 77030, USA Current Address: Community Health System of South Texas, 3135 South Sugar Road, Edinburg, TX 78539, USA E-mail: bimalbanik10@gmail.com, bimal.banik@chsst.org <em>Manuscript received 03 October 2018, accepted 01 Novem

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3

M., S. MANHAS, M. BHAWAL B., B. SHANKAR B. та K. BOSE AJAY. "Stereocontrolled Synthesis of β-Lactams from Amidomalonates : Intermediates for Thienamycin, Carpetimycin and Analogs". Journal of Indian Chemical Society Vol. 62, Nov 1985 (1985): 891–98. https://doi.org/10.5281/zenodo.6325221.

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Department of Chemistry and Chemical Engineering, Stevens Institute of Technology, Hoboken, New Jersey 07080, U.S.A. Complete stereocontrol of<em> β</em>-lactam formation can be achieved by the intra-molecular cyclisation of the epoxide of an <em>N</em>-acroylaminomalonate. The <em>β</em>-lactam so obtained is fused with a lactone ring derived from one of the ester groups of the malonate and the carbinol side chain generated by the sterospecific opening of the epoxide ring. Selective hydrolysis of the lactone group leads to a <em>trans β</em>-lactam ; selective decarbo

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4

Wolfe, Saul, та Tova Hoz. "A semiempirical molecular orbital study of the methanolysis of complex azetidinones. A combined MM and QM analysis of the interaction of Δ2- and Δ3-cephems with the penicillin receptor". Canadian Journal of Chemistry 72, № 4 (1994): 1044–50. http://dx.doi.org/10.1139/v94-132.

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The semiempirical molecular orbital procedures MINDO/3, MNDO, MNDO/M, AM1, and PM3 have been used to examine possible mechanisms and modes of attack of methanol on penam, the bicyclic ring system of penicillin. These mechanisms include a one-step process in which C—O bond formation from the convex face of the molecule and proton transfer to the β-lactam nitrogen are concerted with the cleavage of the N—C(O) bond (the N-protonated pathway), and two O-protonated pathways, viz., addition to the β-lactam carbonyl group from the convex face and from the concave face of the bicyclic ring system. Onl

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5

Shankar, B. B., M. P. Kirkup, S. W. McCombie, J. W. Clader та A. K. Ganguly. "Synthesis of an optically pure 3-unsubstituted β-lactam using an asymmetric Reformatsky reaction and its conversion to cholesterol absorption inhibitors". Tetrahedron Letters 37, № 24 (1996): 4095–98. http://dx.doi.org/10.1016/0040-4039(96)00764-2.

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6

SHANKAR, B. B., M. P. KIRKUP, S. W. MCCOMBIE, J. W. CLADER та A. K. GANGULY. "ChemInform Abstract: Synthesis of an Optically Pure 3-Unsubstituted β-Lactam Using an Asymmetric Reformatsky Reaction and Its Conversion to Cholesterol Absorption Inhibitors." ChemInform 27, № 37 (2010): no. http://dx.doi.org/10.1002/chin.199637150.

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7

Dugat, Denise, George Just та Soumya Sahoo. "β-Lactams. XII.: A study of the synthesis of N-unsubstituted β-lactams, and of 4-styryl monobactams". Canadian Journal of Chemistry 65, № 1 (1987): 88–93. http://dx.doi.org/10.1139/v87-014.

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A few types of amines XNH2 were investigated for the formation of β-lactams via the cycloaddition of the corresponding Schiff bases with azidoacetyl chloride. Among the β-lactams formed, only the N-p,p′-dimethoxybenzhydryl compounds could be transformed to N-unsubstituted azetidinones by removal of the N-substituent with ceric ammonium nitrate. Conversion of those N-unsubstituted intermediates to 3-acylated monobactams was studied in the 4-styryl series.

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8

Banik, Bimal K., Anjan Ghatak та Frederick F. Becker. "Indium-mediated facile synthesis of 3-unsubstituted β-lactams". Journal of the Chemical Society, Perkin Transactions 1, № 14 (2000): 2179–81. http://dx.doi.org/10.1039/b002833i.

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9

Cossío, Fernando P., та Claudio Palomo. "A novel synthetic approach to N-unsubstituted β-lactams". Tetrahedron Letters 26, № 35 (1985): 4235–38. http://dx.doi.org/10.1016/s0040-4039(00)99001-4.

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10

Alcaide, Benito, Alberto Rodríguez-Vicente та Miguel A. Sierra. "A New Radical Route to C4-Unsubstituted β-Lactams". Tetrahedron Letters 39, № 1-2 (1998): 163–66. http://dx.doi.org/10.1016/s0040-4039(97)10476-2.

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11

Zarei, Maaroof, та Aliasghar Jarrahpour. "Synthesis of N-unsubstituted β-lactams from N-alkoxyphenyl-β-lactams with cobalt(III) fluoride". Tetrahedron Letters 51, № 44 (2010): 5791–94. http://dx.doi.org/10.1016/j.tetlet.2010.08.101.

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12

Cainelli, Gianfranco, Daria Giacomini, Mauro Panunzio, Giorgio Martelli та Giuseppe Spunta. "β-lactams from esters and silylimines: A revaluation. Synthesis of N-unsubstituted 4-alkyl-β-lactams". Tetrahedron Letters 28, № 44 (1987): 5369–72. http://dx.doi.org/10.1016/s0040-4039(00)96733-9.

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13

Zarei, Maaroof, та Aliasghar Jarrahpour. "ChemInform Abstract: Synthesis of N-Unsubstituted β-Lactams from N-Alkoxyphenyl-β-lactams with Cobalt(III) Fluoride." ChemInform 42, № 6 (2011): no. http://dx.doi.org/10.1002/chin.201106120.

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14

ALCAIDE, B., A. RODRIGUEZ-VICENTE та M. A. SIERRA. "ChemInform Abstract: A New Radical Route to C4-Unsubstituted β-Lactams." ChemInform 29, № 15 (2010): no. http://dx.doi.org/10.1002/chin.199815095.

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15

Banik, Bimal K., Anjan Ghatak та Frederick F. Becker. "ChemInform Abstract: Indium-Mediated Facile Synthesis of 3-Unsubstituted β-Lactams." ChemInform 31, № 47 (2000): no. http://dx.doi.org/10.1002/chin.200047106.

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16

Ghatak, Anjan, Frederick F. Becker та Bimal K. Banik. "ChemInform Abstract: Indium-Mediated Facile Synthesis of 3-Unsubstituted Ferrocenyl β-Lactams." ChemInform 32, № 11 (2001): no. http://dx.doi.org/10.1002/chin.200111170.

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17

Dasgupta, Swapan K., та Bimal K. Banik. "A new entry to N-unsubstituted β-lactams through a solid-phase approach". Tetrahedron Letters 43, № 51 (2002): 9445–47. http://dx.doi.org/10.1016/s0040-4039(02)02236-0.

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18

White, James D., Steven T. Perri та Steven G. Toske. "Nitrosative deamination of 1-aminoazetidin-2-ones. An entry to N-unsubstituted β-lactams". Tetrahedron Letters 33, № 4 (1992): 433–36. http://dx.doi.org/10.1016/s0040-4039(00)93960-1.

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19

Georg, Gunda I., Ping He, Joydeep Kant та Jeffrey Mudd. "N-vinyl and N-unsubstituted β-lactams from 1-substituted 2-aza-1, 3-butadienes". Tetrahedron Letters 31, № 4 (1990): 451–54. http://dx.doi.org/10.1016/0040-4039(90)87005-k.

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20

Cossfo, Fernando P., Jesûs M. Aizpurua, and Claudio Palomo. "Synthetic applications of chromium(VI) reagents in combination with chlorotrimethylsilane." Canadian Journal of Chemistry 64, no. 2 (1986): 225–31. http://dx.doi.org/10.1139/v86-039.

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The synthetic utility of chromium(VI) reagents together with chlorotrimethylsilane, as new oxidizing systems, is described. Pyridinium dichromate (PDC) in combination with chlorotrimethylsilane oxidizes tert-butyldimethylsilyl ethers in good to excellent yields. Trimethylsilyl chlorochromate, a new chromium(VI) reagent, also was found efficient for this oxidative-deprotection method. These reagents were applied to the oxidation of some N-(2-phenyl-2-hydroxyethyl)azetidin-2-ones as well as N-(2-phenyl-2-trialkylsiloxy)azetidin-2-ones into their corresponding carbonyl compounds, key intermediate

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21

Karupaiyan, K., V. Srirajan, A. R. A. S. Deshmukh та B. M. Bhawal. "Synthesis of N1-unsubstituted β-lactams via a facile deprotection of N1-[(α-thiophenyl)benzyl] group". Tetrahedron 54, № 17 (1998): 4375–86. http://dx.doi.org/10.1016/s0040-4020(98)00151-3.

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22

Karupaiyan, K., V. Srirajan, A. R. A. S. Deshmukh та B. M. Bhawal. "Synthesis of N1-unsubstituted β-lactams: Introducing N1-(1′-thiophenyl)benzyl as an N-protecting group". Tetrahedron Letters 38, № 24 (1997): 4281–84. http://dx.doi.org/10.1016/s0040-4039(97)00879-4.

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23

WHITE, J. D., S. T. PERRI та S. G. TOSKE. "ChemInform Abstract: Nitrosative Deamination of 1-Aminoazetidin-2-ones. An Entry to N- Unsubstituted β-Lactams." ChemInform 23, № 35 (2010): no. http://dx.doi.org/10.1002/chin.199235167.

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24

KARUPAIYAN, K., V. SRIRAJAN, A. R. A. S. DESHMUKH та B. M. BHAWAL. "ChemInform Abstract: Synthesis of N1-Unsubstituted β-Lactams: Introducing N1-(1′- Thiophenyl)benzyl as an N-Protecting Group." ChemInform 28, № 37 (2010): no. http://dx.doi.org/10.1002/chin.199737134.

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25

KARUPAIYAN, K., V. SRIRAJAN, A. R. A. S. DESHMUKH та B. M. BHAWAL. "ChemInform Abstract: Synthesis of N1-Unsubstituted β-Lactams via a Facile Deprotection of N1-[(α-Thiophenyl)benzyl] Group." ChemInform 29, № 30 (2010): no. http://dx.doi.org/10.1002/chin.199830118.

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26

Palomo, Claudio, Jesus M. Aizpurua, Regina Galarza та ін. "On the Question of the Diastereoselective Alkylation of 4-Unsubstituted 3-Amino β-Lactams. A Concise Synthesis of α-Branched α-Amino β-Lactams and their Coupling with α-Amino Acid Esters". Tetrahedron 56, № 31 (2000): 5563–70. http://dx.doi.org/10.1016/s0040-4020(00)00406-3.

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27

Palomo, Claudio, Jesus M. Aizpurua, Regina Galarza та ін. "ChemInform Abstract: The Question of the Diastereoselective Alkylation of 4-Unsubstituted 3-Amino β-Lactams. A Concise Synthesis of α-Branched α-Amino β-Lactams and Their Coupling with α-Amino Acid Esters." ChemInform 31, № 47 (2000): no. http://dx.doi.org/10.1002/chin.200047102.

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28

Alcaide, Benito, Javier Pérez-Castells, Belén Sánchez-Vigo та Miguel A. Sierra. "Hexacarbonyl dicobalt complexed N-pro-2-ynyl-2-azetidinones: a new entry to N-unsubstituted-β-lactams through a Nicholas-type reaction". J. Chem. Soc., Chem. Commun., № 5 (1994): 587–88. http://dx.doi.org/10.1039/c39940000587.

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29

Palomo, Claudio, Fernando P. Cossío, Jesús M. Ontoria та José M. Odriozola. "Preparation of chiral 3-unsubstituted β-lactams from 3-hydroxy β-lactams by using the alkoxyketene-imine cycloaddition reaction as an approach to the azetidinone ring: A formal synthesis of the carbapenem antibiotic (+)-PS-5." Tetrahedron Letters 32, № 26 (1991): 3105–8. http://dx.doi.org/10.1016/0040-4039(91)80701-7.

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30

Gordon, Kirsteen H., та Shankar Balasubramanian. "Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides". Organic Letters 3, № 1 (2001): 53–56. http://dx.doi.org/10.1021/ol006766l.

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31

Gordon, Kirsteen H., та Shankar Balasubramanian. "Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides". Organic Letters 3, № 10 (2001): 1591. http://dx.doi.org/10.1021/ol015940i.

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32

ALCAIDE, B., L. CASARRUBIOS, G. DOMINGUEZ та M. A. SIERRA. "ChemInform Abstract: Iminodithiocarbonates as Formaldehyde Imine Equivalents: Sequential Two Step Approach to 4-Unsubstituted β-Lactams Through Chromium(0) Carbene Photocycloaddition-Nickel Boride Desulfurization." ChemInform 26, № 26 (2010): no. http://dx.doi.org/10.1002/chin.199526103.

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33

GEORG, G. I., P. HE, J. KANT та Z. WU. "ChemInform Abstract: Stereocontrolled Synthesis of N-Vinyl-, N-(1′-Propenyl)-, and N- Unsubstituted β-Lactams from 2-Aza-1,3-butadienes via the Staudinger Reaction." ChemInform 25, № 6 (2010): no. http://dx.doi.org/10.1002/chin.199406125.

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34

ALCAIDE, B., J. PEREZ-CASTELLS, B. SANCHEZ-VIGO та M. A. SIERRA. "ChemInform Abstract: Hexacarbonyl Dicobalt Complexed N-Prop-2-ynyl-2-azetidinones: A New Entry to N-Unsubstituted-β-lactams Through a Nicholas-Type Reaction." ChemInform 25, № 27 (2010): no. http://dx.doi.org/10.1002/chin.199427276.

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35

Georg, Gunda I., Joydeep Kant, Ping He, Ana Maria Ly та Lynn Lampe. "2-aza-1,3-dienes as novel precursors for the synthesis of -unsubstituted β-lactams. A three step synthesis of 4-acetoxy-3-phenoxy-2-azeridinone". Tetrahedron Letters 29, № 20 (1988): 2409–12. http://dx.doi.org/10.1016/s0040-4039(00)87894-6.

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36

Kolkenbrock, Stephan, Katja Parschat, Bernd Beermann, Hans-Jürgen Hinz та Susanne Fetzner. "N-Acetylanthranilate Amidase from Arthrobacter nitroguajacolicus Rü61a, an α/β-Hydrolase-Fold Protein Active towards Aryl-Acylamides and -Esters, and Properties of Its Cysteine-Deficient Variant". Journal of Bacteriology 188, № 24 (2006): 8430–40. http://dx.doi.org/10.1128/jb.01085-06.

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ABSTRACT N-acetylanthranilate amidase (Amq), a 32.8-kDa monomeric amide hydrolase, is involved in quinaldine degradation by Arthrobacter nitroguajacolicus Rü61a. Sequence analysis and secondary structure predictions indicated that Amq is related to carboxylesterases and belongs to the α/β-hydrolase-fold superfamily of enzymes; inactivation of (His6-tagged) Amq by phenylmethanesulfonyl fluoride and diethyl pyrocarbonate and replacement of conserved residues suggested a catalytic triad consisting of S155, E235, and H266. Amq is most active towards aryl-acetylamides and aryl-acetylesters. Remark

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37

PALOMO, C., F. P. COSSIO, J. M. ONTORIA та J. M. ODRIOZOLA. "ChemInform Abstract: Preparation of Chiral 3-Unsubstituted β-Lactams from 3-Hydroxy . beta.-Lactams by Using the Alkoxyketene-Imine Cycloaddition Reaction as an Approach to the Azetidinone Ring: A Formal Synthesis of the Carbapenem Antibiotic (+)-PS-5 (I)". ChemInform 23, № 15 (2010): no. http://dx.doi.org/10.1002/chin.199215312.

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38

Campomanes, Pablo, M. Isabel Menéndez та Tomás L. Sordo. "Theoretical Study of the Mechanism of the Formation of 3-Unsubstituted 4,4-Disubstituted β-Lactams by Silver-Induced Ring Expansion of Alkoxycyclopropylamines: A New Synthetic Route to 4-Alkoxycarbonyl-4-alkyl-2-azetidinones". Journal of Organic Chemistry 68, № 17 (2003): 6685–89. http://dx.doi.org/10.1021/jo034803r.

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39

PFAENDLER, H. R., та H. HOPPE. "ChemInform Abstract: A NOVEL PREPARATION OF 4-UNSUBSTITUTED β-LACTAMS". Chemischer Informationsdienst 16, № 27 (1985). http://dx.doi.org/10.1002/chin.198527177.

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40

OVERMAN, L. E., та T. OSAWA. "ChemInform Abstract: A CONVENIENT SYNTHESIS OF 4-UNSUBSTITUTED β-LACTAMS". Chemischer Informationsdienst 16, № 30 (1985). http://dx.doi.org/10.1002/chin.198530191.

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41

SHARMA, S. D., U. MEHRA, J. P. S. KHURANA та S. B. PANDHI. "ChemInform Abstract: Synthesis of 4-Unsubstituted β-Lactams via Dithiocarbonimidates." ChemInform 19, № 13 (1988). http://dx.doi.org/10.1002/chin.198813174.

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42

Williams, David R., Andrew F. Donnell та David C. Kammler. "Aldol Reactions of Unsubstituted β-Lactams. Studies of a β-Glycine Enolate Equivalent." ChemInform 35, № 19 (2004). http://dx.doi.org/10.1002/chin.200419096.

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43

CAINELLI, G., D. GIACOMINI, M. PANUNZIO, G. MARTELLI та G. SPUNTA. "ChemInform Abstract: β-Lactams from Esters and Silylimines: A Revaluation. Synthesis of N-Unsubstituted 4-Alkyl-β-lactams." ChemInform 19, № 14 (1988). http://dx.doi.org/10.1002/chin.198814177.

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44

DUGAT, D., G. JUST та S. SAHOO. "ChemInform Abstract: β-Lactams. Part 12. A Study of the Synthesis of N-Unsubstituted β-Lactams, and of 4-Styryl Monobactams." ChemInform 18, № 39 (1987). http://dx.doi.org/10.1002/chin.198739151.

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45

GEORG, G. I., P. HE, J. KANT та J. MUDD. "ChemInform Abstract: N-Vinyl and N-Unsubstituted β-Lactams from 1-Substituted 2-Aza-1,3-butadienes." ChemInform 21, № 39 (1990). http://dx.doi.org/10.1002/chin.199039160.

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46

COSSIO, F. P., та C. PALOMO. "ChemInform Abstract: Considered as Reagents and Synthetic Methods. Part 50. A Novel Synthetic Approach to N-Unsubstituted β-Lactams." Chemischer Informationsdienst 17, № 5 (1986). http://dx.doi.org/10.1002/chin.198605170.

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47

ARRIETA, A., B. LECEA, F. P. COSSIO та C. PALOMO. "ChemInform Abstract: Reagents and Synthetic Methods. Part 67. Preparation of 4-Unsubstituted β-Lactams from 4-Acetoxyazetidin-2-ones. A Formal Approach to Monobactams and Nocardicins." ChemInform 20, № 6 (1989). http://dx.doi.org/10.1002/chin.198906152.

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48

GEORG, G. I., J. KANT, P. HE, A. M. LY та L. LAMPE. "ChemInform Abstract: 2-Aza-1,3-dienes as Novel Precursors for the Synthesis of N-Unsubstituted β-Lactams. A Three Step Synthesis of 4-Acetoxy-3-phenoxy-2-azetidinone." ChemInform 19, № 43 (1988). http://dx.doi.org/10.1002/chin.198843171.

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