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

Scholarly Works

• Price, L.; Li, Z.; Zhang, W. Synthesis of a pyrroloquinoline-containing polycyclic scaffold via decarboxylative [3+2] cycloaddition and aza-Wittig reactions. New Journal of Chemistry 2025, 49, 18970–18973. doi:10.1039/d5nj03128a
• Qiu, W.; Zhan, D.; Ma, X.; Zhang, X. 2-Azidobenzaldehyde-Enabled Construction of Quinazoline Derivatives: A Review. International journal of molecular sciences 2025, 26, 8955. doi:10.3390/ijms26188955
• López‐Francés, A.; Diop, B.; Jiang, X.; Rodriguez, J.; Amatore, M.; Constantieux, T. Advances in Enaminomaleimides Chemistry: Synthesis, Chemical Applications, and Perspectives. ChemistryEurope 2025, 3. doi:10.1002/ceur.202500220
• Shen, L.-W.; Lei, S.-L.; Wang, H.-Y.; Wang, X.; Lu, L.-M.; Wang, G.-W.; Jia, Y.-Q.; Xiang, M. Metal-free amination of alkenes based on maleimides. Organic & biomolecular chemistry 2025, 23, 3865–3869. doi:10.1039/d5ob00201j
• Luo, W.; Zheng, X.; Lin, H.; Fu, L.; Long, L.; Yu, D.; Chen, Z.; Yang, M.; Wang, Z.-X. Discovery of intermolecular cascade annulation for dihydrobenzo[b][1,8]naphthyridine-ylidene-pyrrolidinetriones. Chemical science 2025, 16, 4119–4126. doi:10.1039/d4sc07999j
• 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

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