Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
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Benjamin Prek
Abstract
The thermal metal-free [2+2] cycloadditions of electron-poor acetylenes to some polysubstituted systems with conjugated double bonds (polysubstituted butadienes) are described.
Acknowledgment
We are grateful for the financial support from the Slovenian Research Agency, Slovenia, through grants P1-0175 and P1-0179. We acknowledge with thanks the financial support from the pharmaceutical company KRKA, d.d., Novo mesto, Slovenia. We thank EN-FIST Centre of Excellence, Trg OF 13, 1000 Ljubljana, Slovenia, for using the SuperNova diffractometer.
References
[1] B. Stanovnik, Org. Prep. Proced. Int.2014, 46, 24.10.1080/00304948.2014.866468Suche in Google Scholar
[2] J. Bezenšek, T. Koleša, U. Grošelj, A. Meden, K. Stare, J. Svete, B. Stanovnik, Curr. Org. Chem.2011, 15, 2530.10.2174/138527211796150633Suche in Google Scholar
[3] J. Bezenšek, T. Koleša, U. Grošelj, J. Wagger, K. Stare, A. Meden, J. Svete, B. Stanovnik, Tetrahedron Lett.2010, 51, 3392.10.1016/j.tetlet.2010.04.106Suche in Google Scholar
[4] F. Bohlmann, D. Rahtz, Chem. Ber.1957, 90, 2265.10.1002/cber.19570901021Suche in Google Scholar
[5] M. C. Bagley, J. W. Dale, J. Bower, Synlett2001, 1149.10.1055/s-2001-15140Suche in Google Scholar
[6] J. Bezenšek, B. Prek, U. Grošelj, M. Kasunič, J. Svete, B. Stanovnik, Tetrahedron2012, 68, 4719.10.1016/j.tet.2012.04.013Suche in Google Scholar
[7] G. Maas, B. Singer, P. Wald, M. Gimmy, Chem. Ber.1988, 121, 1847.10.1002/cber.19881211025Suche in Google Scholar
[8] R. Rahm, G. Maas, Chem. Ber.1994, 127, 1295.10.1002/cber.19941270719Suche in Google Scholar
[9] K. Drandarov, I. Tiritiris, O. Wassiljew, H.-U. Siehl, W. Kantlehner, Chem. Eur. J.2011, 18, 7224.10.1002/chem.201103695Suche in Google Scholar PubMed
[10] J. Bezenšek, B. Prek, U. Grošelj, A. Golobič, K. Stare, J. Svete, W. Kantlehner, G. Maas, B. Stanovnik, Z. Naturforsch.2014, 69b, 554.10.5560/znb.2014-4021Suche in Google Scholar
[11] B. Prek, J. Bezenšek, M. Kasunič, U. Grošelj, J. Svete, B. Stanovnik, Tetrahedron2014, 70, 2359.10.1016/j.tet.2014.02.039Suche in Google Scholar
[12] B. Prek, U. Grošelj, M. Kasunič, S. Zupančič, J. Svete, B. Stanovnik, Aust. J. Chem.2015, 68, 184.10.1071/CH14349Suche in Google Scholar
[13] B. Prek, J. Bezenšek, B. Stanovnik, Tetrahedron2017, 73, 5260, and references cited therein.10.1016/j.tet.2017.07.019Suche in Google Scholar
[14] J. Bezenšek, B. Prek, U. Grošelj, M. Počkaj, J. Svete, B. Stanovnik, Tetrahedron2015, 71, 7209.10.1016/j.tet.2015.03.008Suche in Google Scholar
[15] J. Bezenšek, U. Grošelj, M. Počkaj, J. Svete, B. Stanovnik, Tetrahedron Lett. 2015, 56, 5705.10.1016/j.tetlet.2015.09.013Suche in Google Scholar
[16] M. Kiesel, E. Haug, W. Kantlehner, J. Prakt. Chem. 1997, 339, 159–170.10.1002/prac.19973390130Suche in Google Scholar
[17] W. Kantlehner, M. Vettel, H. Lehmann, K. Edelmann, R. Stieglitz, I. C. Ivanov, J. Prakt. Chem. 1998, 340, 408.10.1002/prac.19983400503Suche in Google Scholar
[18] K. Edelmann, Dissertation, Universität Stuttgart, Stuttgart, 1998, p. 103.Suche in Google Scholar
[19] K. Edelmann, Dissertation, Universität Stuttgart, Stuttgart, 1998, p.104.Suche in Google Scholar
[20] W. Kantlehner, H. Lehmann, T. Stahl, W. Kaim, Chem. Ztg. 1991, 115, 183.Suche in Google Scholar
[21] J. Mezger, Dissertation, Universität Stuttgart, Stuttgart, 2002, p. 173.Suche in Google Scholar
[22] H. Lehmann, Dissertation, Universität Stuttgart, Stuttgart, 1991, p. 14.Suche in Google Scholar
[23] T. Sasada, F. Kobayashi, N. Sakai, T. Konakahara, Org. Lett.2009, 11, 2161.10.1021/ol900382jSuche in Google Scholar PubMed
[24] CrysAlis Pro Software System, Intelligent Data Collection and Processing Software for Small Molecule and Protein Crystallography, Agilent Technologies Ltd., Yarnton, Oxfordshire (UK), 2011.Suche in Google Scholar
[25] A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, Sir97, A New Tool for Crystal Structure Determination and Refinement, Bari, Perugia, Rome (Italy), 1997.Suche in Google Scholar
[26] A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.10.1107/S0021889898007717Suche in Google Scholar
[27] L. J. Bourhis, O. V. Dolomanov, R. J. Gildea, J. A. K. Howard, H. Puschmann, Acta Crystallogr.2015, A71, 59.10.1107/S2053273314022207Suche in Google Scholar
[28] G. M. Sheldrick, Shelxl-2014/7, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany), 2013.Suche in Google Scholar
[29] G. M. Sheldrick, Acta Crystallogr.2015, C71, 3.Suche in Google Scholar
[30] C. K. Johnson, M. N. Burnett, Ortep-III (version 1.0.2), Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Rep. ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN (USA), 1996.10.2172/369685Suche in Google Scholar
[31] Windows version: L. J. Farrugia, University of Glasgow, Glasgow, Scotland (UK), 1999.Suche in Google Scholar
[32] L. J. Farrugia, J. Appl. Crystallogr.2012, 45, 849.10.1107/S0021889812029111Suche in Google Scholar
©2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- In this Issue
- Preface
- The role of iminium salts, imines and related compounds in chemistry
- Original Articles
- A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines
- Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena
- Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
- Synthesis of functionalized pyrazole derivatives by regioselective [3+2] cycloadditions of N-Boc-α-amino acid-derived ynones
- Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines
- Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
- Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
- Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction
- Review
- Iminiumsalz-Strukturen bei der durch Pyridoxalphosphat (Vitamin B6) katalysierten Bildung von Aromastoffen und Fehlaromen im Wein
Artikel in diesem Heft
- Frontmatter
- In this Issue
- Preface
- The role of iminium salts, imines and related compounds in chemistry
- Original Articles
- A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines
- Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena
- Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
- Synthesis of functionalized pyrazole derivatives by regioselective [3+2] cycloadditions of N-Boc-α-amino acid-derived ynones
- Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines
- Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
- Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
- Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction
- Review
- Iminiumsalz-Strukturen bei der durch Pyridoxalphosphat (Vitamin B6) katalysierten Bildung von Aromastoffen und Fehlaromen im Wein
