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Journal articles on the topic 'Acetylenic ketones'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Shvartsberg, M. S., and L. G. Fedenok. "Isomerization of ?-acetylenic ketones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 9 (September 1990): 1906–10. http://dx.doi.org/10.1007/bf00958259.

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2

Zanina, A. S., S. I. Shergina, I. E. Sokolov, and I. L. Kotlyarevskii. "Synthesis of acetylenic ketones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 11 (November 1990): 2307–11. http://dx.doi.org/10.1007/bf00958843.

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3

Taniguchi, Mikio, Shozo Kobayashi, Masako Nakagawa, Tohru Hino, and Yoshito Kishi. "β-Halovinyl ketones: Synthesis from acetylenic ketones." Tetrahedron Letters 27, no. 39 (January 1986): 4763–66. http://dx.doi.org/10.1016/s0040-4039(00)85059-5.

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4

Mai, Juri, and Sascha Ott. "The Fascinating World of Phosphanylphosphonates: From Acetylenic Phosphaalkenes to Reductive Aldehyde Couplings." Synlett 30, no. 16 (August 13, 2019): 1867–85. http://dx.doi.org/10.1055/s-0039-1690129.

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This account highlights the versatility of phosphanylphosphonates, which can be used for the preparation of phosphorus-containing π-systems and as reagents for the reductive coupling of carbonyl compounds to alkenes. Phosphanylphosphonates with metal fragments coordinated to the P-lone pair have been known for a long time and they have been used for the synthesis of phosphaalkenes by means of the phospha-Horner–Wadsworth–Emmons reaction. With the original aim of incorporating phosphorus heteroatoms into classical all-carbon ethynylethene scaffolds, we entered the field of phosphanylphosphonates with the discovery that these compounds engage in complex cascade reactions with acetylenic ketones, forming 1,2-oxaphospholes, cumulenes, and bisphospholes. Later, we synthesized the first metal-free phosphanylphosphonate, which reacts with aldehydes to yield phosphaalkenes, but gives phospholones when diacetylenic ketones are used as substrates. In the final part of the account, we outline our discovery and the development of an unprecedented carbonyl–carbonyl cross-coupling reaction. This protocol offers a straightforward method for the synthesis of nonsymmetric 1,2-disubstituted alkenes directly from two dissimilar aldehydes.1 Combining Acetylenes with Phosphaalkenes2 Synthetic Examples of Acetylenic Phosphaalkenes3 The Phospha-Horner–Wadsworth–Emmons Approach to Phosphaalkenes3.1 Metal-Coordinated Phosphanylphosphonates3.2 Mechanism of the Phospha-Horner–Wadsworth–Emmons Reaction3.3 The First Metal-Free Phosphanylphosphonate and Its Reactivity with Aldehydes4 Reactions with Acetylenic Ketones4.1 Metal-Coordinated Phosphanylphosphonate and Monoacetylenic Ketones4.2 Metal-Coordinated Phosphanylphosphonate and Diacetylenic Ketones4.3 Metal-Free Phosphanylphosphonate and Diacetylenic Ketones5 Metal-Free Phosphanylphosphonate as a Coupling Reagent for Aldehydes6 E-Alkenes by the Reductive Coupling of Two Aldehydes7 Conclusions and Outlook

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5

Meng, Ling‐Guo, Pei‐Jie Cai, Qing‐Xiang Guo, and Song Xue. "Direct Iodination of Monosubstituted Aryl Acetylenes and Acetylenic Ketones." Synthetic Communications 38, no. 2 (January 2008): 225–31. http://dx.doi.org/10.1080/00397910701749724.

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6

Shergina, S. I., I. E. Sokolov, and A. S. Zanina. "Synthesis of fluorinated acetylenic ketones." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 1 (January 1992): 127–28. http://dx.doi.org/10.1007/bf00863927.

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7

Fukuyama, Takahide, Ryo Yamaura, and Ilhyong Ryu. "Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6." Canadian Journal of Chemistry 83, no. 6-7 (June 1, 2005): 711–15. http://dx.doi.org/10.1139/v05-031.

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A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.Key words: carbonylation, palladium, three-component coupling, ionic liquid, α,β-acetylenic ketones.

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8

Levashov, Andrey S., and Dmitrii S. Buryi. "Tetraalkynylstannanes in Synthesis of α,β-Acetylenic Ketones." Proceedings 9, no. 1 (November 14, 2018): 44. http://dx.doi.org/10.3390/ecsoc-22-05691.

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Akynyl ketones were synthesized from tetraalkinylstannanes and both aliphatic and aromatic acyl chlorides under Lewis acid catalysis. The structure of products was confirmed by means of NMR, IR, GC-MS. The method is suitable for the synthesis of long-chain acetylenic ketones.

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9

Sengee, Myagmarsuren, and Leiv K. Sydnes. "Specific conjugate addition to α,β-acetylenic ketones." Pure and Applied Chemistry 83, no. 3 (February 3, 2011): 587–96. http://dx.doi.org/10.1351/pac-con-10-10-24.

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A variety of α,β-unsaturated acetylenic ketones, prepared in good yields from 3,3,4,4-tetraethoxybut-1-yne (TEB), have been reacted with selected mono- and bis-nucleophilic reagents. The mononucleophiles react in a Michael fashion and give in most cases the corresponding α,β-unsaturated alkenones in good yield. Many of the alkenes are formed as single stereoisomers, but the configuration depends on the nature of the nucleophile. If hydrogen bonds can be formed, the Z geometry is preferred, otherwise the E geometry is completely predominant. Experiments have also uncovered that α,β-unsaturated acetylenic ketones with a gem-diethoxy moiety in the α' position decompose when reacted with sodium hydroxide in aqueous tetrahydrofuran (THF); the carbonyl group is attacked and a carboxylic acid and a terminal alkyne are formed. If the nucleophiles contain two nucleophilic centers or if the α,β-unsaturated acetylenic ketones contain an additional reactive group, such as a hydroxyl group or an acyloxy moiety, useful secondary reactions may occur. By taking advantage of such secondary transformations, two completely regioselective syntheses of furans have so far been developed.

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10

ZANINA, A. S., S. I. SHERGINA, I. E. SOKOLOV, and I. L. KOTLYAREVSKII. "ChemInform Abstract: Synthesis of Acetylenic Ketones." ChemInform 23, no. 27 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199227139.

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11

Levashov, Andrey S., Nicolai A. Aksenov, Inna V. Aksenova, and Valeriy V. Konshin. "Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones." New Journal of Chemistry 41, no. 16 (2017): 8297–304. http://dx.doi.org/10.1039/c7nj01376k.

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12

Youssef, Ahmed Said Ahmed. "Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones." Journal of Chemical Research 2009, no. 4 (April 2009): 214–17. http://dx.doi.org/10.3184/030823409x435874.

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Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile (1a) with substituted benzylidenemalononitriles gave 4-amino-2-(1-cyano-2-arylvinyl)benzothieno[2,3- d]pyrimidine derivatives (3) as ( E,Z)-mixtures and in one case (2c) as separated ( Z)- and ( E)-isomers. Similar treatment of 6-amino-1,4-dihydro-3-methyl-1,4-diphenyl-pyrano[2,3- c]pyrazole-5-carbonitrile (4) yielded similarly-formed pyrazolopyranopyrimidine derivatives (5a, b) as ( Z)-and ( E)-stereoisomers. Attempted acetylation of the aminobenzothienopyrimidines resulted in degradation of the pyrimidine ring and the formation of N-(3-cyano-4,5,6,7-tetrahydro[1]benzothien-2-yl)acetamide (1b). Treatment of 4 with acetylenic esters and ketones (6a-d) afforded the ( Z)-substituted enaminopyrano[2,3- c]pyrazole derivatives. Reacting 1a with aroyl phenyl acetylenes gave by Michael addition the enamino-ketones (8a-c).

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13

SHVARTSBERG, M. S., and L. G. FEDENOK. "ChemInform Abstract: Isomerization of α-Acetylenic Ketones." ChemInform 22, no. 39 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199139088.

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14

Fang, Zhijia, and Martin Wills. "Asymmetric Transfer Hydrogenation of Functionalized Acetylenic Ketones." Journal of Organic Chemistry 78, no. 17 (August 15, 2013): 8594–605. http://dx.doi.org/10.1021/jo401284c.

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15

Wang, Jin-Xian, Bangguo Wei, Zhanxiang Liua, Hu Yulai, and Liqing Kang. "A Convenient Synthesis of Conjugated Acetylenic Ketones by Copper(I)-Catalysis under Microwave Irradiation." Journal of Chemical Research 2001, no. 4 (April 2001): 146–47. http://dx.doi.org/10.3184/030823401103169306.

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16

Kallepu, Shivakrishna, Krishna Kumar Gollapelli, Jagadeesh Babu Nanubolu, and Rambabu Chegondi. "Synthesis of highly strained bicyclic[3.n.1]alkenes by a metal-catalyzed Conia-ene reaction." Chemical Communications 51, no. 94 (2015): 16840–43. http://dx.doi.org/10.1039/c5cc05926g.

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17

Gollapelli, Krishna Kumar, Shivakrishna Kallepu, Nagendra Govindappa, Jagadeesh Babu Nanubolu, and Rambabu Chegondi. "Carbonyl-assisted reverse regioselective cascade annulation of 2-acetylenic ketones triggered by Ru-catalyzed C–H activation." Chemical Science 7, no. 7 (2016): 4748–53. http://dx.doi.org/10.1039/c6sc01456a.

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The first reverse regioselective intermolecular annulation of aryl substituted 2-acetylenic ketones with O-substituted N-hydroxybenzamides or acrylamides followed by tandem cyclization via ruthenium-catalyzed C–H activation, is reported.

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18

SHERGINA, S. I., I. E. SOKOLOV, and A. S. ZANINA. "ChemInform Abstract: Synthesis of Fluorine-Containing Acetylenic Ketones." ChemInform 25, no. 3 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199403108.

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19

Matsumura, Kazuhiko, Shohei Hashiguchi, Takao Ikariya, and Ryoji Noyori. "Asymmetric Transfer Hydrogenation of α, β-Acetylenic Ketones." Journal of the American Chemical Society 119, no. 37 (September 1997): 8738–39. http://dx.doi.org/10.1021/ja971570a.

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20

Li, Pei, Wai Man Fong, Lisa C. F. Chao, Stephen H. C. Fung, and Ian D. Williams. "A Convenient Synthesis of α,β-Acetylenic Ketones." Journal of Organic Chemistry 66, no. 11 (June 2001): 4087–90. http://dx.doi.org/10.1021/jo015534c.

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21

Harding, Charles E., and Salane L. King. "Mechanism of the intramolecular cyclization of acetylenic ketones." Journal of Organic Chemistry 57, no. 3 (January 1992): 883–86. http://dx.doi.org/10.1021/jo00029a019.

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22

Verkruijsse, H. D., Y. A. Heus-Kloos, and L. Brandsma. "Efficient methods for the preparation of acetylenic ketones." Journal of Organometallic Chemistry 338, no. 3 (January 1988): 289–94. http://dx.doi.org/10.1016/0022-328x(88)80002-0.

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23

Komarova, T. N., A. S. Nakhmanovich, M. V. Sigalov, and T. E. Glotova. "The reaction of terminal ?-acetylenic ketones with thiosemicarbazones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 5 (May 1990): 1058–60. http://dx.doi.org/10.1007/bf00961717.

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24

Mosslemin, Mohammad H., Mohammad Anary-Abbassinejad, Alireza Hassanabadi, Marzieh Mohebat, and Mohammad R. Nateghi. "Reaction Between Triphenylphosphine and Acetylenic Esters or Acetylenic Ketones in the Presence of Mercaptoesters." Synthetic Communications 39, no. 19 (September 4, 2009): 3482–92. http://dx.doi.org/10.1080/00397910902778027.

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25

Elokhina, V. N., T. I. Yaroshenko, A. S. Nakhmanovich, L. I. Larina, and S. V. Amosova. "Reaction of dithiomalonic acid dianilide with substituted acetylenic ketones." Russian Journal of General Chemistry 76, no. 12 (December 2006): 1916–18. http://dx.doi.org/10.1134/s1070363206120140.

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26

Drewes, Siegfried E., Deborah Douglass, Dean G. S. Malissar, Gregory H. P. Roos, and Perry T. Kaye. "Reactivity and reactions of aromatic acetylenic acids and ketones." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1990): 1507. http://dx.doi.org/10.1039/p19900001507.

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27

Degl'Innocenti, Alessandro, Antonella Capperucci, Gianna Reginato, Alessandro Mordini, and Alfredo Ricci. "Reactivity of acetylenic silyl ketones: synthesis of functionalized propenoylsilanes." Tetrahedron Letters 33, no. 11 (March 1992): 1507–8. http://dx.doi.org/10.1016/s0040-4039(00)91660-5.

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28

Shergina, Sophia I., Ivan E. Sokolov, and Alevtina S. Zanina. "A Facile Method of Synthesis of α-Acetylenic Ketones." Mendeleev Communications 4, no. 6 (January 1994): 207. http://dx.doi.org/10.1070/mc1994v004n06abeh000415.

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29

Holla, B. Shivarama, K. Venkatramana Udupa, and K. R. Sridhar. "The Reaction of α,β-Acetylenic Ketones with Aroylhydrazines." Bulletin of the Chemical Society of Japan 62, no. 10 (October 1989): 3409–11. http://dx.doi.org/10.1246/bcsj.62.3409.

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30

Ananchenko, G. S., A. A. Petrov, and B. A. Ershov. "ChemInform Abstract: Addition of Phenylhydrazine to α-Acetylenic Ketones." ChemInform 30, no. 49 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199949115.

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31

Fang, Zhijia, and Martin Wills. "ChemInform Abstract: Asymmetric Transfer Hydrogenation of Functionalized Acetylenic Ketones." ChemInform 45, no. 5 (January 16, 2014): no. http://dx.doi.org/10.1002/chin.201405042.

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32

Manandhar, Sudha, Rajendra P. Singh, and Jean'ne M. Shreeve. "Fluoride-Catalyzed Nucleophilic Perfluoroalkylations of Acetylenic Ketones or Aldehydes." Collection of Czechoslovak Chemical Communications 67, no. 9 (2002): 1296–304. http://dx.doi.org/10.1135/cccc20021296.

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Reactions of 4-phenylbut-3-yn-2-one (1a) and phenylpropynal (1b) with trimethyl(perfluoroalkyl)silanes (Me3SiRf) (Rf = CF3, C2F5, n-C6F13, n-C7F15, n-C8F17) in the presence of catalytic amounts of cesium fluoride (CsF) have been studied. Compounds 1a, 1b were reacted with 0.5 equivalent excess of Me3SiRf in ethylene glycol dimethyl ether (monoglyme) at 25 °C for Rf = CF3, C2F5 and at 50 °C for Rf = n-C6F13, n-C7F15, n-C8F17 to give the corresponding perfluoroalkylated alcohols in good yields after acid hydrolysis. The new compounds were characterized by IR, NMR (1H, 19F, 13C), MS and elemental analysis. In these reactions, tetrabutylammonium fluoride (TBAF) is also effective as the fluoride catalyst. The alcohols with CF3 or C2F5 are viscous liquids whereas those with n-C6F13, n-C7F15 or n-C8F17 are solids. They are soluble in common organic solvents and stable to air and moisture.

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33

Ranu, Brindaban C., Sanjay Bhar, and Ratna Chakraborti. "Synthesis of .beta.-keto 1,3-dithianes from acetylenic ketones." Journal of Organic Chemistry 57, no. 26 (December 1992): 7349–52. http://dx.doi.org/10.1021/jo00052a064.

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34

GAO, Jun-Li, Yong-Kang LIU, and Song XUE. "Self-condensation of Terminal Acetylenic Ketones via Organozinc Species." Chinese Journal of Chemistry 26, no. 9 (September 2008): 1689–92. http://dx.doi.org/10.1002/cjoc.200890305.

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35

Sheng, Huaiyu, Shouyuan Lin, and Yaozeng Huang. "A novel palladium-catalyzed rearrangement of acetylenic ketones to furans." Tetrahedron Letters 27, no. 40 (January 1986): 4893–94. http://dx.doi.org/10.1016/s0040-4039(00)85090-x.

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36

Masquelin, T., and D. Obrecht. "A novel access to 2,4-substituted quinolines from acetylenic ketones." Tetrahedron 53, no. 2 (January 1997): 641–46. http://dx.doi.org/10.1016/s0040-4020(96)01025-3.

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37

Al-Hajjar, Farouk S., and Salim S. Sabri. "Reaction of acetylenic ketones with hydrazine derivatives. Synthesis of hydroxypyrazoles." Journal of Heterocyclic Chemistry 23, no. 3 (May 1986): 727–29. http://dx.doi.org/10.1002/jhet.5570230317.

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38

Li, Pei, Wai Man Fong, Lisa C. F. Chao, Stephen H. C. Fung, and Ian D. Williams. "ChemInform Abstract: A Convenient Synthesis of α,β-Acetylenic Ketones." ChemInform 32, no. 42 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200142092.

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39

Sengee, Myagmarsuren, and Leiv K. Sydnes. "ChemInform Abstract: Specific Conjugate Addition to α,β-Acetylenic Ketones." ChemInform 43, no. 2 (December 15, 2011): no. http://dx.doi.org/10.1002/chin.201202235.

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40

KANDEEL, K. A., J. M. VERNON, T. A. DRANSFIELD, F. A. FOULI, and A. S. A. YOUSSEF. "ChemInform Abstract: Reactions of Malononitrile with Acetylenic Esters and Ketones." ChemInform 22, no. 5 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199105098.

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41

KOMAROVA, T. N., A. S. NAKHMANOVICH, M. V. SIGALOV, and T. E. GLOTOVA. "ChemInform Abstract: Reaction of Terminal α-Acetylenic Ketones with Thiosemicarbazones." ChemInform 22, no. 6 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199106176.

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42

MATSUMURA, K., S. HASHIGUCHI, T. IKARIYA, and R. NOYORI. "ChemInform Abstract: Asymmetric Transfer Hydrogenation of α,β-Acetylenic Ketones." ChemInform 28, no. 51 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199751079.

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43

HOLLA, B. S., and K. SHRIDHARA. "ChemInform Abstract: Reactions of Aryloxyacetylhydrazines with α,β-Acetylenic Ketones." ChemInform 23, no. 21 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199221181.

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44

Hamed, Ezzat A., Saber M. Sharaf, Samy A. Abdel-Baky, Mahmoud F. Ibrahim, and Abdel-Hamid A. Youssef. "Stereochemistry and kinetics of addition of amines to acetylenic ketones." Journal of Physical Organic Chemistry 3, no. 10 (October 1990): 627–34. http://dx.doi.org/10.1002/poc.610031002.

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45

Maas, Gerhard, Martin Reisser, and Alexandra Maier. "Addition Reactions of Tertiary Silylphosphanes with Acetylenic Ketones and Aldehydes." Synlett 2002, no. 9 (2002): 1459–62. http://dx.doi.org/10.1055/s-2002-33533.

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46

Rao, V. Bhaskar, Steven Wolff, and William C. Agosta. "Novel cyclization of type II biradicals from .alpha.,.beta.-acetylenic ketones." Journal of the American Chemical Society 107, no. 2 (January 1985): 521–22. http://dx.doi.org/10.1021/ja00288a051.

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47

Wei, Han-Xun, Jiali Hu, David W. Purkiss, and Paul W. Paré. "Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2." Tetrahedron Letters 44, no. 5 (January 2003): 949–52. http://dx.doi.org/10.1016/s0040-4039(02)02746-6.

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48

Smith, III, Amos B., Patricia A. Levenberg, and Joan Z. Suits. "Chromium (II) Reagents; 1. Reduction of α-Acetylenic Ketones totrans-Enones." Synthesis 1986, no. 03 (1986): 184–89. http://dx.doi.org/10.1055/s-1986-31616.

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49

RANU, B. C., S. BHAR, and R. CHAKRABORTI. "ChemInform Abstract: Synthesis of β-Keto 1,3-Dithianes from Acetylenic Ketones." ChemInform 24, no. 20 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199320227.

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50

YOUSSEF, A. S. A., K. A. KANDEEL, and H. M. F. MADKOUR. "ChemInform Abstract: Reactions of Carbon-Nucleophiles with Acetylenic Esters and Ketones." ChemInform 27, no. 21 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199621051.

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