Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2004, 69, 945-965
https://doi.org/10.1135/cccc20040945

Electronic Effects on the Bergman Cyclisation of Enediynes. A Review

Michael Klein, Thomas Walenzyk and Burkhard König*

Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany

Crossref Cited-by Linking

  • Cai Yue, Binder Wolfgang H.: Triggered Crosslinking of Main‐Chain Enediyne Polyurethanes via Bergman Cyclization. Macromol. Rapid Commun. 2023, 44. <https://doi.org/10.1002/marc.202300440>
  • Bhattacharya Prabuddha, Chakraborty Soham, Balaji Ashwin, Basak Amit: Angle distortion model for predicting enediyne activation towards Bergman cyclization: an alternate to the distance theory. RSC Adv. 2022, 12, 23552. <https://doi.org/10.1039/D2RA03193K>
  • Singha Monisha, Bhattacharya Prabuddha, Ray Debashis, Basak Amit: Sterically hindering the trajectory of nucleophilic attack towards p-benzynes by a properly oriented hydrogen atom: an approach to achieve regioselectivity. Org. Biomol. Chem. 2021, 19, 5148. <https://doi.org/10.1039/D1OB00521A>
  • Janiszewski Alexandra, Fax Jonas, Haberhauer Gebhard: Dimerization of substituted 4-aryl-1,3-diacetylenes – quantum chemical calculations and kinetic studies. Org. Chem. Front. 2019, 6, 1010. <https://doi.org/10.1039/C9QO00119K>
  • Lyapunova Anna G., Danilkina Natalia A., Rumyantsev Andrey M., Khlebnikov A. F., Chislov Mikhail V., Starova Galina L., Sambuk Elena V., Govdi Anastasia I., Bräse Stefan, Balova Irina A.: Relative Reactivity of Benzothiophene-Fused Enediynes in the Bergman Cyclization. J. Org. Chem. 2018, 83, 2788. <https://doi.org/10.1021/acs.joc.7b03258>
  • Das Eshani, Basak Shyam, Anoop Anakuthil, Basak Amit: Experiment and Computational Study on the Regioselectivity of Nucleophilic Addition to Unsymmetrical p-Benzynes Derived from Bergman Cyclization of Enediynes. J. Org. Chem. 2018, 83, 7730. <https://doi.org/10.1021/acs.joc.8b00624>
  • Fabig Sven, Janiszewski Alexandra, Floß Martin, Kreuzahler Mathis, Haberhauer Gebhard: Dimerization of Substituted Arylacetylenes—Quantum Chemical Calculations and Kinetic Studies. J. Org. Chem. 2018, 83, 7878. <https://doi.org/10.1021/acs.joc.8b00755>
  • Bhattacharya Prabuddha, Basak Amit, Campbell Adam, Alabugin Igor V.: Photochemical Activation of Enediyne Warheads: A Potential Tool for Targeted Antitumor Therapy. Mol. Pharmaceutics 2018, 15, 768. <https://doi.org/10.1021/acs.molpharmaceut.7b00911>
  • Wang Youfu, Chen Shudan, Hu Aiguo: Construction of Polyarylenes with Various Structural Features via Bergman Cyclization Polymerization. Top Curr Chem (Z) 2017, 375. <https://doi.org/10.1007/s41061-017-0145-4>
  • Chen Shudan, Hu Aiguo: Recent advances of the Bergman cyclization in polymer science. Sci. China Chem. 2015, 58, 1710. <https://doi.org/10.1007/s11426-015-5460-4>
  • Saxena Aakarsh, Perez Felix, Krische Michael J.: Ruthenium(0) Catalyzed Endiyne−α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C–C Bond Forming Transfer Hydrogenation. J. Am. Chem. Soc. 2015, 137, 5883. <https://doi.org/10.1021/jacs.5b02755>
  • Wu Weirong, Bi Siwei, Liu Yuxia, Tang Yanan, Li Bingwen: Insight into Pd-catalyzed branching cyclizations of enediyne-imides towards furo[2,3-b]pyridines: a DFT study. Org. Biomol. Chem. 2015, 13, 11539. <https://doi.org/10.1039/C5OB01991E>
  • Kraka Elfi, Cremer Dieter: Enediynes, enyne‐allenes, their reactions, and beyond. WIREs Comput Mol Sci 2014, 4, 285. <https://doi.org/10.1002/wcms.1174>
  • Danilkina N. A., Kulyashova A. E., Khlebnikov A. F., Bräse S., Balova I. A.: Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core. J. Org. Chem. 2014, 79, 9018. <https://doi.org/10.1021/jo501396s>
  • Peterson Paul W., Mohamed Rana K., Alabugin Igor V.: How to Lose a Bond in Two Ways ― The Diradical/Zwitterion Dichotomy in Cycloaromatization Reactions. Eur J Org Chem 2013, 2013, 2505. <https://doi.org/10.1002/ejoc.201201656>
  • Rossi Renzo, Bellina Fabio, Lessi Marco, Manzini Chiara: Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes. Tetrahedron 2013, 69, 7869. <https://doi.org/10.1016/j.tet.2013.06.002>
  • Mohamed Rana K., Peterson Paul W., Alabugin Igor V.: Concerted Reactions That Produce Diradicals and Zwitterions: Electronic, Steric, Conformational, and Kinetic Control of Cycloaromatization Processes. Chem. Rev. 2013, 113, 7089. <https://doi.org/10.1021/cr4000682>
  • Breiner Boris, Kaya Kemal, Roy Saumya, Yang Wang-Yong, Alabugin Igor V.: Hybrids of amino acids and acetylenic DNA-photocleavers: optimising efficiency and selectivity for cancer phototherapy. Org. Biomol. Chem. 2012, 10, 3974. <https://doi.org/10.1039/c2ob00052k>
  • Laroche Christophe, Li Jing, Kerwin Sean M.: Cytotoxic 1,2-Dialkynylimidazole-Based Aza-Enediynes: Aza-Bergman Rearrangement Rates Do Not Predict Cytotoxicity. J. Med. Chem. 2011, 54, 5059. <https://doi.org/10.1021/jm200289j>
  • Poloukhtine Andrei, Rassadin Valentin, Kuzmin Alexander, Popik Vladimir V.: Nucleophilic Cycloaromatization of Ynamide-Terminated Enediynes. J. Org. Chem. 2010, 75, 5953. <https://doi.org/10.1021/jo101238x>
  • Laroche Christophe, Li Jing, Gonzales Cristina, David Wendi M., Kerwin Sean M.: Cyclization kinetics and biological evaluation of an anticancer 1,2-dialkynylimidazole. Org. Biomol. Chem. 2010, 8, 1535. <https://doi.org/10.1039/b925261d>
  • García‐García Patricia, Fernández‐Rodríguez Manuel A., Aguilar Enrique: Gold‐Catalyzed Cycloaromatization of 2,4‐Dien‐6‐yne Carboxylic Acids: Synthesis of 2,3‐Disubstituted Phenols and Unsymmetrical Bi‐ and Terphenyls. Angewandte Chemie 2009, 121, 5642. <https://doi.org/10.1002/ange.200901269>
  • García‐García Patricia, Fernández‐Rodríguez Manuel A., Aguilar Enrique: Gold‐Catalyzed Cycloaromatization of 2,4‐Dien‐6‐yne Carboxylic Acids: Synthesis of 2,3‐Disubstituted Phenols and Unsymmetrical Bi‐ and Terphenyls. Angew Chem Int Ed 2009, 48, 5534. <https://doi.org/10.1002/anie.200901269>
  • Mitra Debarati, Sengupta Arjun, Biradha Kumar, Basak Amit: Asymmetric cyclopropanation using amino acid as chiral auxiliary. Tet Asymm 2008, 19, 2678. <https://doi.org/10.1016/j.tetasy.2008.11.009>
  • Watanabe Masataka, Shiine Kodai, Ideta Keiko, Matsumoto Taisuke, Thiemann Thies: Diene-yne cyclisation reactions of 1-ethynyl-2-vinyl-3,4-dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes. Journal of Chemical Research 2008, 2008, 669. <https://doi.org/10.3184/030823408X375214>
  • Sahu Bichismita, Muruganantham Rajendran, Namboothiri Irishi N. N.: Synthetic and Mechanistic Investigations on the Rearrangement of 2,3‐Unsaturated 1,4‐Bis(alkylidene)carbenes to Enediynes. Eur J Org Chem 2007, 2007, 2477. <https://doi.org/10.1002/ejoc.200601137>
  • Kar Moumita, Basak Amit: Design, Synthesis, and Biological Activity of Unnatural Enediynes and Related Analogues Equipped with pH-Dependent or Phototriggering Devices. Chem. Rev. 2007, 107, 2861. <https://doi.org/10.1021/cr068399i>
  • Poloukhtine Andrei, Popik Vladimir V.: Synthesis and Unusual Reactivity of N-Tosyl-4,5-benzoazacyclodeca-2,6-diyne, Yneamino-Containing Enediyne. J. Am. Chem. Soc. 2007, 129, 12062. <https://doi.org/10.1021/ja073614d>
  • Hayama Tomoharu, Wu Yao-Ting, Linden Anthony, Baldridge Kim K., Siegel Jay S.: Synthesis, Structure, and Isomerization of Decapentynylcorannulene:  Enediyne Cyclization/Interconversion of C40R10 Isomers. J. Am. Chem. Soc. 2007, 129, 12612. <https://doi.org/10.1021/ja074403b>
  • Sherman Courtney L., Pierce Sarah E., Brodbelt Jennifer S., Tuesuwan Bodin, Kerwin Sean M.: Identification of the adduct between a 4-aza-3-ene-1,6-diyne and DNA using electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 2006, 17, 1342. <https://doi.org/10.1016/j.jasms.2006.05.015>
  • Nielsen Mogens Brøndsted, Diederich François: Conjugated Oligoenynes Based on the Diethynylethene Unit. Chem. Rev. 2005, 105, 1837. <https://doi.org/10.1021/cr9903353>
  • O'Connor Joseph M., Friese Seth J., Rodgers Betsy L.: A Transition-Metal-Catalyzed Enediyne Cycloaromatization. J. Am. Chem. Soc. 2005, 127, 16342. <https://doi.org/10.1021/ja050060a>
  • Morgan Kathleen M.: 11  Reaction mechanisms : Part (iii) Pericyclic reactions. Annu. Rep. Prog. Chem., Sect. B 2005, 101, 284. <https://doi.org/10.1039/b500185b>
  • Klein Michael, Walenzyk Thomas, Koenig Burkhard: Electronic Effects on the Bergman Cyclization of Enediynes. ChemInform 2004, 35. <https://doi.org/10.1002/chin.200439240>