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Journal articles on the topic 'Cyclobutenediones'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Allen, Annette D., Jim D. Colomvakos, Ian Egle, et al. "1995 R.U. Lemieux Award Lecture Ketenes and bisketeness: organic chemistry in microcosm." Canadian Journal of Chemistry 74, no. 4 (1996): 457–64. http://dx.doi.org/10.1139/v96-050.

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Silyl substituents stabilize ketenes, and permit the preparation of persistent bisketenes, which show characteristic 13C, 17O, and 29Si NMR chemical shifts. The structures and conformations of bisketenes have been examined, as well as their interconversion with cyclobutenediones. A tetraketene has been prepared, and the hydration reactivity of carbon suboxide has been measured. Key words: bisketenes, structures and conformations; cyclobutenedione interconversion.

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2

Liu, Ronghua, and Thomas T. Tidwell. "A stabilized and persistent tetraketene: 1,4-bis(1′,4′-dioxo-3′-trimethylsilyl-2′-buta-1′,3′-dienyl)benzene." Canadian Journal of Chemistry 73, no. 11 (1995): 1818–22. http://dx.doi.org/10.1139/v95-224.

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Reaction of 1,4-bis(trimethylsilylethynyl)benzene with CCl3COCl and Zn gave 1,4-bis(4′,4′-dichloro-2′-trimethylsilyl-3′-oxo-1′-cyclobutenyl)benzene (7), which reacted with concentrated H2SO4 at 87 °C to give 1,4-bis(2′-trimethylsilyl-3′,4′-dioxo-1′-cyclobutenyl)benzene (8). Photolysis of 8 in CDCl3 with 350 nm light gave the bisketene 9, which on further photolysis formed the title tetraketene 10, as identified by its spectral properties. Upon heating of 10 the successive closure of the two bisketene moieties, first to give the mono(cyclobutenedione) 9 and then to reform 8 in a slower step, wa

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3

Wang, Pengcheng, Ruirui Yu, Sajjad Ali, et al. "Silver Catalyzed Decarbonylative [3 + 2] Cycloaddition of Cyclobutenediones and Formamides." Molecules 26, no. 10 (2021): 2974. http://dx.doi.org/10.3390/molecules26102974.

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As an important moiety in natural products, N,O-acetal has attracted wide attention in the past few years. An efficient method to construct N,O-acetal has been developed. Using silver catalyst, cyclobutenediones were smoothly converted to the corresponding γ-aminobutenolides in the presence of formamides, in which cyclobutenediones likely proceed with a key decarbonylative [3 + 2] cycloaddition process. In this way, a series of products with varied substituents were isolated in moderate yield and fully characterized.

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4

Schaumann, Ernst, Gerrit Oppermann, Michael Stranberg, and Harold W. Moore. "New Syntheses and Ring Expansion Reactions of Cyclobutenimines." Australian Journal of Chemistry 63, no. 12 (2010): 1656. http://dx.doi.org/10.1071/ch10318.

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Two routes are reported for the synthesis of iminocyclobutenones having N-(het)aryl substitution: an addition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein’s reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give 4-aminophenols, 4-amino-1-naphthols, or

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5

Fu, Nanyan, Annette D. Allen, Winnie Chan, et al. "Generation, observation, and reactivity of furyl- and thienylketenes and bisketenes." Canadian Journal of Chemistry 86, no. 4 (2008): 333–41. http://dx.doi.org/10.1139/v08-021.

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2- and 3-Furylketenes (18 and 20), 2- and 3-thienylketenes (19 and 21), and bis(2,5-ketenyl)thiophene (24) have been generated as observable reactive intermediates by photochemical Wolff rearrangements. Stabilization energies of the monoketenes 18–21 have been determined by DFT computations of isodesmic energy changes, and these ketenes are predicted to be modestly destabilized relative to phenylketene. Rate constants for reaction of 18–21 with H2O and with n-BuNH2 have been measured and are similar to those of the 2-, 3-, and 4-pyridylketenes (1). The product of reaction of 2-furylketene (18)

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6

Avalos, Javier, Harold W. Moore, Michael W. Reed, and Eloy Rodriguez. "Sensitizing potential of cyclobutenediones." Contact Dermatitis 21, no. 5 (1989): 341–42. http://dx.doi.org/10.1111/j.1600-0536.1989.tb04757.x.

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7

Lee, Kwan Hee, and Harold W. Moore. "Unusual Transformation of Cyclobutenediones into Butenolides." Journal of the Korean Chemical Society 47, no. 3 (2003): 229–36. http://dx.doi.org/10.5012/jkcs.2003.47.3.229.

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8

Bennett, Ryan M., Wei Sun, Dharyl C. Wilson, Mark E. Light, and David C. Harrowven. "A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans." Chemical Communications 57, no. 46 (2021): 5694–97. http://dx.doi.org/10.1039/d1cc02097h.

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The addition of lithium amides to cyclobutenediones provides access to 2-oxo-but-3-enamides and tetrasubstituted furans via a new mode of ring opening involving enone cleavage via O- to C-lithium transfer.

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9

Mukkanti, Amere, and Mariappan Periasamy. "Methods of synthesis of cyclobutenediones." Arkivoc 2005, no. 11 (2004): 48–77. http://dx.doi.org/10.3998/ark.5550190.0006.b07.

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10

Petasis, Nicos A., and Dian-Kui Fu. "Synthesis of Substituted Benzonorbornadienes from Cyclobutenediones." Synlett 1996, no. 02 (1996): 155–56. http://dx.doi.org/10.1055/s-1996-5351.

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11

Liebeskind, Lanny S. "Cyclobutenediones as precursors to quinones and cyclopentenones." Tetrahedron 45, no. 10 (1989): 3053–60. http://dx.doi.org/10.1016/s0040-4020(01)80131-9.

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12

Liebeskind, Lanny S., and Richard W. Fengl. "3-Stannylcyclobutenediones as nucleophilic cyclobutenedione equivalents. Synthesis of substituted cyclobutenediones and cyclobutenedione monoacetals and the beneficial effect of catalytic copper iodide on the Stille reaction." Journal of Organic Chemistry 55, no. 19 (1990): 5359–64. http://dx.doi.org/10.1021/jo00306a012.

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13

Periasamy, Mariappan, та Mallesh Beesu. "Stereoselective γ-Olefination of Substituted Cyclobutenediones by Organocatalysis". Synlett 2011, № 19 (2011): 2834–40. http://dx.doi.org/10.1055/s-0031-1289879.

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14

Zora, Metin, Baris Yucel, and N. Bekir Peynircioglu. "Coupling of ferrocenyl chromium carbene complex with cyclobutenediones." Journal of Organometallic Chemistry 656, no. 1-2 (2002): 11–17. http://dx.doi.org/10.1016/s0022-328x(02)01403-1.

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15

Liebeskind, Lanny S., and Jing Zhang. "Synthesis of quinolinoquinones and 1,2,3,4-tetrahydroquinolinoquinones via cyclobutenediones." Journal of Organic Chemistry 56, no. 22 (1991): 6379–85. http://dx.doi.org/10.1021/jo00022a031.

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16

PETASIS, N. A., and D. K. FU. "ChemInform Abstract: Synthesis of Substituted Benzonorbornadienes from Cyclobutenediones." ChemInform 27, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199625091.

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17

LIEBESKIND, L. S., and R. W. FENGL. "ChemInform Abstract: 3-Stannylcyclobutenediones as Nucleophilic Cyclobutenedione Equivalents. Synthesis of Substituted Cyclobutenediones and Cyclobutenedione Monoacetals and the Beneficial Effect of Catalytic Copper Iodide on the Stille Reaction." ChemInform 22, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199108147.

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18

Sun, Lijun, and Lanny S. Liebeskind. "Construction of Highly-Substituted Aromatics Bearing Acyl Substituents Using Cyclobutenedione Technology: Vinylketene-Based Benzannulations Using 3-Acyl-4-(substituted amino)cyclobutenediones." Journal of Organic Chemistry 60, no. 25 (1995): 8194–203. http://dx.doi.org/10.1021/jo00130a018.

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19

Liebeskind, Lanny S., Richard W. Fengl, Kevin R. Wirtz, and Thomas T. Shawe. "An improved method for the synthesis of substituted cyclobutenediones." Journal of Organic Chemistry 53, no. 11 (1988): 2482–88. http://dx.doi.org/10.1021/jo00246a017.

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20

Schmidt, Arthur H., Timo Schreck, Ralf Rötz, and Sarah von Freytag-Loringhoven. "Oxokohlenstoffe und verwandte Verbindungen, 30 [1]. Über die Umsetzung von Quadratsäure mit Pyrazolinonen / Oxocarbons and Related Compounds, 30 [1]. On the Reaction of Squaric Acid with Pyrazolinones." Zeitschrift für Naturforschung B 61, no. 3 (2006): 311–19. http://dx.doi.org/10.1515/znb-2006-0311.

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Abstract Heating of squaric acid (1) with the 1-aryl-3-methyl-5-oxo-2,5-dihydro-1H-pyrazoles 3a - j and the 1,3-disubstituted pyrazolinones 7a - d in the molar ratio of 1:2 in a mixture of n-BuOH/toluene afforded the bis(pyrazolyl)-squaraines 4a - j and 8a - d, respectively. Reaction of an excess of 1 with the pyrazolinone 3j yielded 4j and the 3-hydroxy-4-pyrazolyl-cyclobutene-1,2-dione 6 as a byproduct. In contrast to disubstituted pyrazolinones, the trisubstituted pyrazolinones 9a - e reacted with squaric acid (1) to give the hydroxy-oxopyrazolyl-cyclobutenediones 10a - e.

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21

Mallesh, Beesu, and Periasamy Mariappan. "Reactive iron carbonyl reagents for conversion of alkynes to cyclobutenediones, cyclic imides and anhydrides via double carbonylation." Journal of Indian Chemical Society Vol. 90, Oct 2013 (2013): 1795–803. https://doi.org/10.5281/zenodo.5792043.

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School of Chemistry, University of Hyderabad, Central University P.O., Hyderabad-500 046, India <em>E-mail </em>: mpsc@uohyd.ernet.in <em>Manuscript received 06 August 2013, accepted 07 August 2013</em> Methods have been developed for the preparation of reactive iron carbonyl reagents for dicarbonylation of alkynes under various reaction conditions. In most cases, the cyclobutenediones were obtained in moderate to good yields (27-93%). In some cases, the iron carbonyl intermediates were converted to the corresponding benzoquinones (51-80%), cyclicimides (45-65%) and cyclic anhydrides (60-80%)

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22

Fu, Nanyan, Annette D. Allen, Shinjiro Kobayashi, et al. "Structural Effects on Interconversion of Oxygen-Substituted Bisketenes and Cyclobutenediones." Journal of Organic Chemistry 73, no. 5 (2008): 1768–73. http://dx.doi.org/10.1021/jo702312t.

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23

Beesu, Mallesh, та Mariappan Periasamy. "ChemInform Abstract: Stereoselective γ-Olefination of Substituted Cyclobutenediones by Organocatalysis." ChemInform 43, № 15 (2012): no. http://dx.doi.org/10.1002/chin.201215043.

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24

LIEBESKIND, L. S., and J. ZHANG. "ChemInform Abstract: Synthesis of Quinolinequinones and 1,2,3,4-Tetrahydroquinolinequinones via Cyclobutenediones." ChemInform 23, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199217188.

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25

SUN, L., and L. S. LIEBESKIND. "ChemInform Abstract: Construction of Highly-Substituted Aromatics Bearing Acyl Substituents Using Cyclobutenedione Technology: Vinylketene-Based Benzannulations Using 3-Acyl-4-(substituted amino)cyclobutenediones." ChemInform 27, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199618051.

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26

Rameshkumar, Chellappan, and Mariappan Periasamy. "Amine induced carbonylation of alkynes to cyclobutenediones using Fe3(CO)12." Tetrahedron Letters 41, no. 15 (2000): 2719–22. http://dx.doi.org/10.1016/s0040-4039(00)00247-1.

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27

Packard, Emma, David D. Pascoe, Jacques Maddaluno, Théo P. Gonçalves, and David C. Harrowven. "Organoytterbium Ate Complexes Extend the Value of Cyclobutenediones as Isoprene Equivalents." Angewandte Chemie 125, no. 49 (2013): 13314–17. http://dx.doi.org/10.1002/ange.201307193.

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28

Packard, Emma, David D. Pascoe, Jacques Maddaluno, Théo P. Gonçalves, and David C. Harrowven. "Organoytterbium Ate Complexes Extend the Value of Cyclobutenediones as Isoprene Equivalents." Angewandte Chemie International Edition 52, no. 49 (2013): 13076–79. http://dx.doi.org/10.1002/anie.201307193.

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29

BOTTARI, P. Q., and M. A. BATTISTE. "ChemInform Abstract: Cyclobutenediones as Versatile Four-Carbon Synthons in Organic Synthesis." ChemInform 29, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.199851333.

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30

Allen, Annette D., and Thomas T. Tidwell. "Ring opening of cyclobutene-1,2-dione and 3-trimethylsilylcyclobutene-1,2-dione. Dimerization/decarbonylation of a bisketene to a ketenylbutenolide." Canadian Journal of Chemistry 77, no. 5-6 (1999): 802–5. http://dx.doi.org/10.1139/v99-040.

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Hydrolysis of 3-trimethylsilyl-4,4-dichlorocyclobut-2-ene-1-one (4) in H2SO4 gave small amounts of cyclobutene-1,2-dione (2a) and 3-trimethylsilylcyclobutene-1,2-dione (2d). Photolysis of 2a gave evidence for the formation of the bisketene (CH=C=O2) (1a) in solution for the first time, as identified by the IR band at 2120 cm-1 and the 1H NMR signal at δ 3.20. Thermolysis of 2d gave evidence for the intermediacy of O=C=CHC(SiMe3)=C=O (1d), with an 1H NMR signal at δ 3.43, and the isolation of the unusual ketenyl lactone 6, which could arise by formation of an unsymmetrical [2+2] ketene dimer fr

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31

Periasamy, Mariappan, Amere Mukkanti, and D. Shyam Raj. "Novel Synthesis of Acyloxyferrole Complexes from Alkynes and Their Conversion to Cyclobutenediones." Organometallics 23, no. 3 (2004): 619–21. http://dx.doi.org/10.1021/om0341395.

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32

Liu, Ronghua, and Thomas T. Tidwell. "Aryl substituent effects on the thermal interconversion of cyclobutenediones and 1,2-bisketenes." Journal of the Chemical Society, Perkin Transactions 2, no. 12 (1996): 2757. http://dx.doi.org/10.1039/p29960002757.

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33

Allen, Annette D., Jim D. Colomvakos, Ian Egle, et al. "Kinetic and Theoretical Studies of Ring Closure of Unstabilized Bisketenes to Cyclobutenediones." Journal of the American Chemical Society 117, no. 28 (1995): 7552–53. http://dx.doi.org/10.1021/ja00133a032.

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34

Xu, Simon, Benjamin R. Yerxa, Robert W. Sullivan, and Harold W. Moore. "Synthesis of substituted cyclobutenediones from 3-ethenyl-4-methoxy-cyclobutene-1,2-dione." Tetrahedron Letters 32, no. 9 (1991): 1129–32. http://dx.doi.org/10.1016/s0040-4039(00)92025-2.

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35

Mingo, Pamela, Shijie Zhang та Lanny S. Liebeskind. "One-Step Synthesis of Substituted α-Pyrones from Cyclobutenediones and LithiatedO-Silyl Cyanohydrins". Journal of Organic Chemistry 64, № 6 (1999): 2145–48. http://dx.doi.org/10.1021/jo982271m.

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36

Sun, Lijun, and Lanny S. Liebeskind. "2-(Alkylamino)-4-cyclopentene-1,3-diones via Addition of Imidoyl Lithiates to Cyclobutenediones." Journal of Organic Chemistry 59, no. 22 (1994): 6856–58. http://dx.doi.org/10.1021/jo00101a058.

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37

Liebeskind, Lanny S., Kenneth L. Granberg, and Jing Zhang. "A strategy for generalization of the regiospecific synthesis of substituted quinones from cyclobutenediones." Journal of Organic Chemistry 57, no. 16 (1992): 4345–52. http://dx.doi.org/10.1021/jo00042a009.

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38

XU, S., B. R. YERXA, R. W. SULLIVAN, and H. W. MOORE. "ChemInform Abstract: Synthesis of Substituted Cyclobutenediones from 3-Ethenyl-4- methoxycyclobutene-1,2-dione." ChemInform 22, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199152135.

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39

Rameshkumar, Chellappan, and Mariappan Periasamy. "ChemInform Abstract: Amine-Induced Carbonylation of Alkynes to Cyclobutenediones Using Fe3(CO)12." ChemInform 31, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.200026078.

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40

Liebeskind, Lanny S., and Jianying Wang. "Synthesis of substituted cyclobutenediones by the palladium catalyzed cross-coupling of halocyclobutenediones with organostannanes." Tetrahedron Letters 31, no. 30 (1990): 4293–96. http://dx.doi.org/10.1016/s0040-4039(00)97604-4.

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41

Periasamy, Mariappan, Amere Mukkanti, and D. Shyam Raj. "Synthesis of Cyclobutenediones and Anhydrides from Alkynes Using the Fe(CO)5/Me3NO Reagent System." Organometallics 23, no. 26 (2004): 6323–26. http://dx.doi.org/10.1021/om049429f.

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42

Chao, Jianhua, Arthur G. Taveras, Jianping Chao, et al. "C(4)-alkyl substituted furanyl cyclobutenediones as potent, orally bioavailable CXCR2 and CXCR1 receptor antagonists." Bioorganic & Medicinal Chemistry Letters 17, no. 13 (2007): 3778–83. http://dx.doi.org/10.1016/j.bmcl.2007.04.016.

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43

Zhang, Dawei, Isidro Llorente, and Lanny S. Liebeskind. "Versatile Synthesis of Dihydroquinolines and Quinoline Quinones Using Cyclobutenediones. Construction of the Pyridoacridine Ring System." Journal of Organic Chemistry 62, no. 13 (1997): 4330–38. http://dx.doi.org/10.1021/jo970039v.

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44

Periasamy, Mariappan, Chellappan Rameshkumar, and Ukkiramapandian Radhakrishnan. "Novel Reaction of the [HFe3(CO)11]− reagent with alkynes: A new synthesis of cyclobutenediones." Tetrahedron Letters 38, no. 41 (1997): 7229–32. http://dx.doi.org/10.1016/s0040-4039(97)01677-8.

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45

SUN, L., and L. S. LIEBESKIND. "ChemInform Abstract: 2-(Alkylamino)-4-cyclopentene-1,3-diones via Addition of Imidoyl Lithiates to Cyclobutenediones." ChemInform 26, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199520084.

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46

LIEBESKIND, L. S., K. L. GRANBERG, and J. ZHANG. "ChemInform Abstract: A Strategy for Generalization of the Regiospecific Synthesis of Substituted Quinones from Cyclobutenediones." ChemInform 23, no. 51 (1992): no. http://dx.doi.org/10.1002/chin.199251164.

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47

Mingo, Pamela, Shijie Zhang та Lanny S. Liebeskind. "ChemInform Abstract: One-Step Synthesis of Substituted α-Pyrones from Cyclobutenediones and Lithiated O-Silyl Cyanohydrins." ChemInform 30, № 29 (2010): no. http://dx.doi.org/10.1002/chin.199929137.

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48

LIEBESKIND, L. S., and J. WANG. "ChemInform Abstract: Synthesis of Substituted Cyclobutenediones by the Palladium-Catalyzed Cross-Coupling of Halocyclobutenediones with Organostannanes." ChemInform 22, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199133132.

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49

Iwata, Shin, Toshiyuki Hamura, and Keisuke Suzuki. "Siloxy(trialkoxy)ethene undergoes regioselective [2+2] cycloaddition to ynones and ynoates en route to functionalized cyclobutenediones." Chemical Communications 46, no. 29 (2010): 5316. http://dx.doi.org/10.1039/c0cc00883d.

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50

Biju, Purakkattle, Arthur G. Taveras, Michael P. Dwyer та ін. "Fluoroalkyl α side chain containing 3,4-diamino-cyclobutenediones as potent and orally bioavailable CXCR2–CXCR1 dual antagonists". Bioorganic & Medicinal Chemistry Letters 19, № 5 (2009): 1431–33. http://dx.doi.org/10.1016/j.bmcl.2009.01.033.

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