Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

Xiaofeng Zhang, Kenny Pham, Shuai Liu, Marc Legris, Alex Muthengi, Jerry P. Jasinski and Wei Zhang
Beilstein J. Org. Chem. 2016, 12, 2204–2210. https://doi.org/10.3762/bjoc.12.211

Supporting Information

Supporting Information File 1: Compound characterization data, X-ray report, and copies of NMR spectra.
Format: PDF Size: 1.9 MB Download

Cite the Following Article

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
Xiaofeng Zhang, Kenny Pham, Shuai Liu, Marc Legris, Alex Muthengi, Jerry P. Jasinski and Wei Zhang
Beilstein J. Org. Chem. 2016, 12, 2204–2210. https://doi.org/10.3762/bjoc.12.211

How to Cite

Zhang, X.; Pham, K.; Liu, S.; Legris, M.; Muthengi, A.; Jasinski, J. P.; Zhang, W. Beilstein J. Org. Chem. 2016, 12, 2204–2210. doi:10.3762/bjoc.12.211

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: 171.7 KB Download

Citations to This Article

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

Scholarly Works

  • Doraghi, F.; Karimian, S.; Aledavoud, S. P.; Amini, A.; Larijani, B.; Mahdavi, M. 2-azidobenzaldehyde: A versatile scaffold for the generation of N‐heterocyclic compounds. Journal of Molecular Structure 2023, 1294, 136510. doi:10.1016/j.molstruc.2023.136510
  • Zhang, W.; Zheng, W.; Zuo, G.; Li, X.; Zhang, X.; Zhang, W. One-pot Mannich/aza-Wittig/deaminative aromatization reactions for the synthesis of 1,2,3,4-tetrahydroacridines and cyclohepta[b]quinolines. New Journal of Chemistry 2022, 47, 220–223. doi:10.1039/d2nj04082d
  • Lu, J.; Yao, B.; Zhan, D.; Sun, Z.; Ji, Y.; Zhang, X. One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles. Beilstein journal of organic chemistry 2022, 18, 1607–1616. doi:10.3762/bjoc.18.171
  • Zhang, X.; Liu, M.; Zhan, D.; Kaur, M.; Jasinski, J. P.; Zhang, W. Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines. New journal of chemistry = Nouveau journal de chimie 2022, 46, 3866–3870. doi:10.1039/d1nj05538k
  • Zhang, X.; Ma, X.; Qiu, W.; Awad, J.; Zhang, W. Double [3 + 2] cycloadditions for diastereoselective synthesis of spirooxindole pyrrolizidines. Green Processing and Synthesis 2022, 11, 1128–1135. doi:10.1515/gps-2022-0088
  • Zhang, W. doi:10.1002/9783527832439.ch5
  • Zhang, X.; Qiu, W.; Murray, S. A.; Zhan, D.; Evans, J.; Jasinski, J. P.; Wang, X.; Zhang, W. Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s. The Journal of organic chemistry 2021, 86, 17395–17403. doi:10.1021/acs.joc.1c01797
  • Zhang, X.; Ma, X.; Qiu, W.; Awad, J. M.; Evans, J.; Zhang, W. One-Pot Mannich, Aza-Wittig and Dehydrofluorinative Aromatization Reactions for Direct Synthesis of 2,3-Disubstituted 4-Aminoquinolines. Advanced Synthesis & Catalysis 2020, 362, 5513–5517. doi:10.1002/adsc.202000734
  • Ma, X.; Zhang, X.; Awad, J. M.; Xie, G.; Qiu, W.; Muriph, R. E.; Zhang, W. Sequential decarboxylative [3+2] cycloaddition and Staudinger/aza-Wittig reactions for diastereoselective synthesis of tetrahydro-pyrroloquinazolines and tetrahedro-pyrrolobenzodiazepines. Tetrahedron Letters 2020, 61, 151392. doi:10.1016/j.tetlet.2019.151392
  • Ma, X.; Zhang, X.; Xie, G.; Awad, J. M.; Zhang, W. One-pot diastereoselective synthesis of tetrahydroepimino-benzo[b]azocines through sequential [3+2]-cycloaddition and Staudinger-aza-Wittig reactions. Tetrahedron Letters 2019, 60, 151127. doi:10.1016/j.tetlet.2019.151127
  • Ma, X.; Zhang, X.; Awad, J. M.; Xie, G.; Qiu, W.; Zhang, W. One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/N-alkylation (N-acylation)/Staudinger/aza-Wittig reactions. Green Chemistry 2019, 21, 4489–4494. doi:10.1039/c9gc01642b
  • Zhang, W.; Yi, W.-B. Multicomponent Reactions (MCRs). SpringerBriefs in Molecular Science; Springer International Publishing, 2019; pp 27–40. doi:10.1007/978-3-030-22596-4_4
  • Zhang, X.; Qiu, W.; Evans, J.; Kaur, M.; Jasinski, J. P.; Zhang, W. Double 1,3-Dipolar Cycloadditions of Two Nonstabilized Azomethine Ylides for Polycyclic Pyrrolidines. Organic letters 2019, 21, 2176–2179. doi:10.1021/acs.orglett.9b00487
  • Zhang, X.; Qiu, W.; Ma, X.; Evans, J.; Kaur, M.; Jasinski, J. P.; Zhang, W. One-Pot Double [3 + 2] Cycloadditions for Diastereoselective Synthesis of Pyrrolidine-Based Polycyclic Systems. The Journal of organic chemistry 2018, 83, 13536–13542. doi:10.1021/acs.joc.8b02046
  • Zhang, X.; Zhang, W. PASE synthesis of pyrrolidine-containing heterocycles through [3+2] cycloaddition-initiated reactions. Current Opinion in Green and Sustainable Chemistry 2018, 11, 65–69. doi:10.1016/j.cogsc.2018.04.005
  • Zhang, X.; Liu, M.; Qiu, W.; Evans, J.; Kaur, M.; Jasinski, J. P.; Zhang, W. One-Pot Synthesis of Polycyclic Spirooxindoles via Montmorillonite K10-Catalyzed C–H Functionalization of Cyclic Amines. ACS Sustainable Chemistry & Engineering 2018, 6, 5574–5579. doi:10.1021/acssuschemeng.8b00555
  • Muthengi, A.; Zhang, X.; Dhawan, G.; Zhang, W.; Corsini, F. M.; Zhang, W. Sequential (3 + 2) cycloaddition and (5 + n) annulation for modular synthesis of dihydrobenzoxazines, tetrahydrobenzoxazepines and tetrahydrobenzoxazocines. Green Chemistry 2018, 20, 3134–3139. doi:10.1039/c8gc01099d
  • Zhang, X.; Liu, M.; Zhang, W.; Legris, M.; Zhang, W. Synthesis of trifluoromethylated pyrrolidines via decarboxylative [3+2] cycloaddition of non-stabilized N-unsubstituted azomethine ylides. Journal of Fluorine Chemistry 2017, 204, 18–22. doi:10.1016/j.jfluchem.2017.10.003
  • Bdiri, B.; Zhao, B.-J.; Zhou, Z. Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles. Tetrahedron: Asymmetry 2017, 28, 876–899. doi:10.1016/j.tetasy.2017.05.010
  • Zhang, X.; Dhawan, G.; Muthengi, A.; Liu, S.; Wang, W.; Legris, M.; Zhang, W. One-pot and catalyst-free synthesis of pyrroloquinolinediones and quinolinedicarboxylates. Green Chemistry 2017, 19, 3851–3855. doi:10.1039/c7gc01380a
Other Beilstein-Institut Open Science Activities