Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1986, 51, 118-127
https://doi.org/10.1135/cccc19860118

Reactions of triterpenoid ketones with sulfur and morpholine under the conditions of Willgerodt-Kindler reaction

Jan Sejbal, Jiří Klinot, Jiří Protiva and Alois Vystrčil

Department of Organic Chemistry, Charles University, 128 40 Prague 2

Crossref Cited-by Linking

  • Brägger Yannick, Green Ori, Bhawal Benjamin N., Morandi Bill: Late-Stage Molecular Editing Enabled by Ketone Chain-Walking Isomerization. J. Am. Chem. Soc. 2023, 145, 19496. <https://doi.org/10.1021/jacs.3c05680>
  • López-Huerta Fabiola A., Ramírez-Apan María Teresa, Méndez-Cuesta Carlos A., Nieto-Camacho Antonio, Hernández-Ortega Simón, Almeida-Aguirre Ericka K.P., Cerbón Marco A., Delgado Guillermo: Synthesis, biological evaluation, molecular docking studies and In-silico ADMET evaluation of pyrazines of pentacyclic triterpenes. Bioorganic Chemistry 2022, 125, 105924. <https://doi.org/10.1016/j.bioorg.2022.105924>
  • Dinh Ngoc Thuc: Synthesis and characterization of some new 1,2,3-thiadiazole and 1,2,3-selenadiazole triterpene derivatives from allobetulone and 2-oxoallobetulin. Synthetic Communications 2020, 50, 1665. <https://doi.org/10.1080/00397911.2020.1750655>
  • Ngoc Thuc Dinh, Dehaen Wim, Meervelt Luc Van, Balzarini Jan: Synthesis of Heterocyclic Triterpene Derivatives with Biological Activities via Click Reaction. COC 2020, 23, 2969. <https://doi.org/10.2174/1385272823666191212110411>
  • Zorina Alla D., Nikiforova Nadezhda S., Zarubaev Vladimir V., Marchenko Sergei A., Selivanov Stanislav I., Starova Galina L., Mehtiev Arif R., Rodionov Evgenii I., Rodionova Alina A., Trifonov Rostislav E.: Synthesis, structure and in vitro biological evaluation of new lupane and dammarane triterpenoids fused with pyrazine heterocycle. Mendeleev Communications 2019, 29, 500. <https://doi.org/10.1016/j.mencom.2019.09.007>
  • Kazakova Oxana B., Khusnutdinova Elmira F., Petrova Anastasiya V., Yamansarov Emil Yu., Lobov Alexander N., Fedorova Alexandra A., Suponitsky Kyrill Yu.: Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by Griesbaum Co-ozonolysis. J. Nat. Prod. 2019, 82, 2550. <https://doi.org/10.1021/acs.jnatprod.9b00393>
  • Zorina A. D., Nikiforova N. S., Starova G. L., Marchenko S. A., Selivanov S. I., Trifonov R. E.: Synthesis and Structure of a New Semisynthetic Taraxerone Derivative Fused to a Pyrazine Ring through the C2–C3 Bond. Russ J Org Chem 2018, 54, 514. <https://doi.org/10.1134/S1070428018030247>
  • Kvasnica Miroslav, Urban Milan, Dickinson Niall J., Sarek Jan: Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance. Nat. Prod. Rep. 2015, 32, 1303. <https://doi.org/10.1039/C5NP00015G>
  • Galaiko N. V., Nazarov A. V., Tolmacheva I. A., Slepukhin P. A., Vikharev Yu. B., Maiorova O. A., Grishko V. V.: Synthesis of Triterpene A-Condensed Azoles. Chem Heterocycl Comp 2014, 50, 65. <https://doi.org/10.1007/s10593-014-1449-8>
  • Dinh Ngoc Thuc, Dehaen Wim: Selective functionalization of 2-oxoallobetulin derivatives. Tetrahedron 2014, 70, 1836. <https://doi.org/10.1016/j.tet.2013.12.075>
  • Pettit George R., Melody Noeleen, Hempenstall Frank, Chapuis Jean-Charles, Groy Thomas L., Williams Lee: Antineoplastic Agents. 595. Structural Modifications of Betulin and the X-ray Crystal Structure of an Unusual Betulin Amine Dimer1. J. Nat. Prod. 2014, 77, 863. <https://doi.org/10.1021/np400947d>
  • Tolmacheva I. A., Grishko V. V., Tolstikov A. G., Voronova L. N.: Synthesis of C2 symmetric triterpene bis-enaminones. Chem Natur Comp 2012, 48, 75. <https://doi.org/10.1007/s10600-012-0162-z>
  • Schnell Gilles, Schaeffer Philippe, Motsch Estelle, Adam Pierre: Triterpenoids functionalized at C-2 as diagenetic transformation products of 2,3-dioxygenated triterpenoids from higher plants in buried wood. Org. Biomol. Chem. 2012, 10, 8276. <https://doi.org/10.1039/c2ob26191j>
  • Orlov A. V., Khazipova G. R., Komissarova N. G., Shitikova O. V., Spirikhin L. V., Yunusov M. S.: Trofimov synthesis of betulin derivatives with 2,3-annelated pyrrole. Chem Nat Compd 2011, 46, 906. <https://doi.org/10.1007/s10600-011-9780-0>
  • Dehaen Wim, Mashentseva Anastassiya A., Seitembetov Talgat S.: Allobetulin and Its Derivatives: Synthesis and Biological Activity. Molecules 2011, 16, 2443. <https://doi.org/10.3390/molecules16032443>
  • Hao Jia, Zhang Pu, Wen Xiaoan, Sun Hongbin: Efficient Access to 2-Isobetulinic Acid, 2-Isooleanolic Acid, and 2-Isoursolic Acid. J. Org. Chem. 2008, 73, 7405. <https://doi.org/10.1021/jo801232s>
  • Urban Milan, Sarek Jan, Kvasnica Miroslav, Tislerova Iva, Hajduch Marian: Triterpenoid Pyrazines and Benzopyrazines with Cytotoxic Activity. J. Nat. Prod. 2007, 70, 526. <https://doi.org/10.1021/np060436d>
  • Weibel Nicolas, Charbonnière Loïc J., Ziessel Raymond F.: Direct Synthesis of Imines from gem-Dibromomethylaryl Derivatives:  Application to Unsymmetrically Substituted Bipyridine Frameworks. J. Org. Chem. 2002, 67, 7876. <https://doi.org/10.1021/jo020260u>
  • SEJBAL J., KLINOT J., PROTIVA J., VYSTRCIL A.: ChemInform Abstract: Triterpenes. Part 73. Reactions of Triterpenoid Ketones with Sulfur and Morpholine Under the Conditions of the Willgerodt‐Kindler Reaction. Chemischer Informationsdienst 1986, 17. <https://doi.org/10.1002/chin.198621290>