New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

Long Zhao, Mao-Lin Yang, Min Liu and Ming-Wu Ding
Beilstein J. Org. Chem. 2022, 18, 286–292. https://doi.org/10.3762/bjoc.18.32

Supporting Information

Supporting Information File 1: Experimental section and copies of NMR spectra.
Format: PDF Size: 6.4 MB Download

Cite the Following Article

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence
Long Zhao, Mao-Lin Yang, Min Liu and Ming-Wu Ding
Beilstein J. Org. Chem. 2022, 18, 286–292. https://doi.org/10.3762/bjoc.18.32

How to Cite

Zhao, L.; Yang, M.-L.; Liu, M.; Ding, M.-W. Beilstein J. Org. Chem. 2022, 18, 286–292. doi:10.3762/bjoc.18.32

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: 9.5 MB Download

Citations to This Article

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

Scholarly Works

  • Nasri, S.; Lestoquoy, M.; Ponchel, A.; Monflier, E.; Menuel, S. Mechanochemical synthesis of β-cyclodextrin urea derivatives under reactive CO2 atmosphere by Staudinger aza-Wittig reaction. RSC Mechanochemistry 2024, 1, 228–234. doi:10.1039/d4mr00020j
  • Luo, Y.; Yu, H.-F.; Yang, L.-N.; Yao, G.; Jin, Y.; Wei, Z.-Q.; Xue, P.; Qin, R.; Li, L.-Q.; Sun, Q.; Xiong, J. Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process. Tetrahedron 2024, 158, 133984. doi:10.1016/j.tet.2024.133984
  • Zhang, X.; Liu, M.; Qiu, W.; Zhang, W. 2-Azidobenzaldehyde-Based [4+2] Annulation for the Synthesis of Quinoline Derivatives. Molecules (Basel, Switzerland) 2024, 29, 1241. doi:10.3390/molecules29061241
  • Zhao, L.; Yang, M.-L.; Chen, H.-R.; Ding, M.-W. New efficient synthesis of polysubstituted benzo[d]pyrido[1′,2':1,2]imidazo[4,5-f][1,3]diazepines and pyrido[2′,1':2,3]imidazo[1,5-c]quinazolin-7-ium salts via Groebke-Blackburn-Bienaymé/Staudinger/aza-Wittig/carbodiimide-mediated annulation sequence. Tetrahedron 2024, 152, 133834. doi:10.1016/j.tet.2024.133834
  • 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
  • Yang, M.-L.; Zhao, L.; Chen, H.-R.; Ding, M.-W. Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction. The Journal of organic chemistry 2023, 88, 16424–16434. doi:10.1021/acs.joc.3c01955
  • Kong, H.; Zhao, L.; Pan, H.; Ding, M. Synthesis of Dibenzo[b,e]azepin‐6(11H)‐ones via a Sequential Ugi‐4CR and Sulfur Ylide‐Mediated Rearrangement Reaction. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300127
  • Yang, M.-L.; Zhao, L.; Chen, H.-R.; Ding, M.-W. Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5H-Quinazolino[3,2-a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization. The Journal of organic chemistry 2023, 88, 1898–1906. doi:10.1021/acs.joc.2c02621
  • Yang, M.-L.; Pan, H.-L.; Kong, H.-H.; Ding, M.-W. One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions. Organic Chemistry Frontiers 2022, 9, 5983–5988. doi:10.1039/d2qo01130a
Other Beilstein-Institut Open Science Activities