Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

Işıl Yenice, Sinan Basceken and Metin Balci
Beilstein J. Org. Chem. 2017, 13, 825–834. https://doi.org/10.3762/bjoc.13.83

Supporting Information

Supporting Information File 1: NMR spectra, X-ray crystallographic data, and Cartesian Coordinates for the optimized structures.
Format: PDF Size: 2.2 MB Download

Cite the Following Article

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties
Işıl Yenice, Sinan Basceken and Metin Balci
Beilstein J. Org. Chem. 2017, 13, 825–834. https://doi.org/10.3762/bjoc.13.83

How to Cite

Yenice, I.; Basceken, S.; Balci, M. Beilstein J. Org. Chem. 2017, 13, 825–834. doi:10.3762/bjoc.13.83

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 352.5 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Li, M.; Song, L.; Yang, L.; Zhao, Y.; Yang, M.; Tao, H. Development of Glycosylation Protocols Using Glycosyl N-Phenylethynyl Pyrrole-2-carboxylates as Donors. Organic letters 2024. doi:10.1021/acs.orglett.4c03768
  • Gangnale, L. D.; Miriyala, S. R. T.; Pasunooti, K. K.; Reddy, D. S. Amidative Cyclization of Alkynyl Esters to Access Pyrazin-1(2H)-ones: Application to the Synthesis of Peramine and Dibromophakellin. The Journal of organic chemistry 2023, 88, 17330–17344. doi:10.1021/acs.joc.3c02157
  • Ivanov, A. V.; Bobkov, A. S.; Martynovskaya, S. V.; Budaev, A. B.; Vitkovskaya, N. M. A Short‐Cut to Substituted Fused Pyrrolo[2,1‐c][1,4]oxazines: A Hybrid Theoretical and Experimental Study. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202300153
  • Kowalczyk, A.; Jasiński, M. 4,5-Dihydro-1,2,4-triazin-6(1H)-ones (microreview). Chemistry of Heterocyclic Compounds 2022, 58, 585–587. doi:10.1007/s10593-022-03138-y
  • Lalli, C. Comprehensive Heterocyclic Chemistry IV - Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Two Extra Heteroatoms 0:2. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 659–684. doi:10.1016/b978-0-12-409547-2.14939-x
  • Mardjan, M. I. D. Comprehensive Heterocyclic Chemistry IV - Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: One Extra Heteroatom 0:1. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 622–658. doi:10.1016/b978-0-12-818655-8.00032-9
  • Dehnavi, F.; Alizadeh, S. R.; Ebrahimzadeh, M. A. Pyrrolopyrazine derivatives: synthetic approaches and biological activities. Medicinal Chemistry Research 2021, 30, 1981–2006. doi:10.1007/s00044-021-02792-9
  • Ghosh, A.; Barik, S.; Barik, S.; Shee, S.; Biju, A. T. Oxidative N-heterocyclic carbene (NHC) catalysis for the rapid access to functionalized pyrrolo-oxazinones. Tetrahedron 2021, 94, 132330. doi:10.1016/j.tet.2021.132330
  • Winant, P.; Horsten, T.; de Melo, S. M. G.; da Silva Emery, F.; Dehaen, W. A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones. Organics 2021, 2, 118–141. doi:10.3390/org2020011
  • Maisto, S. K.; Leersnyder, A. P.; Pudner, G. L.; Scheerer, J. R. Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine. The Journal of organic chemistry 2020, 85, 9264–9271. doi:10.1021/acs.joc.0c01263
  • Balci, M. Recent advances in the synthesis of fused heterocycles with new skeletons via alkyne cyclization. Tetrahedron Letters 2020, 61, 151994. doi:10.1016/j.tetlet.2020.151994
  • Cokol, N. K.; Erden, K.; Gunay, F. M.; Dengiz, C.; Balci, M. Synthesis of thienopyridinones via hydrazide-alkyne cyclization. Tetrahedron 2020, 76, 131151. doi:10.1016/j.tet.2020.131151
  • Habert, L.; Sallio, R.; Durandetti, M.; Gosmini, C.; Gillaizeau, I. Zinc Chloride Mediated Synthesis of 3H‐Oxazol‐2‐one and Pyrrolo‐oxazin‐1‐one from Ynamide. European Journal of Organic Chemistry 2019, 2019, 5175–5179. doi:10.1002/ejoc.201900428
  • Sari, O.; Seybek, A. F.; Kaya, S.; Menges, N.; Erdem, S. S.; Balci, M. Mechanistic Insights into the Reaction of N‐Propargylated Pyrrole‐ and Indole‐Carbaldehyde with Ammonia, Alkyl Amines, and Branched Amines: A Synthetic and Theoretical Investigation. European Journal of Organic Chemistry 2019, 2019, 5261–5274. doi:10.1002/ejoc.201900084
  • Reinus, B. J.; Kerwin, S. M. Preparation and Utility of N-Alkynyl Azoles in Synthesis. Molecules (Basel, Switzerland) 2019, 24, 422. doi:10.3390/molecules24030422
  • Aslanoglu, F.; Basceken, S.; Balci, M. Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives. Tetrahedron Letters 2019, 60, 449–451. doi:10.1016/j.tetlet.2019.01.004
  • Baskın, D.; Çetinkaya, Y.; Balci, M. Synthesis of dipyrrolo-diazepine derivatives via intramolecular alkyne cyclization. Tetrahedron 2018, 74, 4062–4070. doi:10.1016/j.tet.2018.06.013
  • Allmann, T. C.; Moldovan, R.-P.; Jones, P. G.; Lindel, T. Synthesis of Hydroxypyrrolone Carboxamides Employing Selectfluor. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 22, 111–115. doi:10.1002/chem.201503695
Other Beilstein-Institut Open Science Activities