DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives

Soumitra Guin, Raman Gupta, Debashis Majee and Sampak Samanta
Beilstein J. Org. Chem. 2018, 14, 2771–2778. https://doi.org/10.3762/bjoc.14.254

Supporting Information

Supporting Information File 1: Synthetic protocols, characterization data and copies of 1H and 13C NMR spectra.
Format: PDF Size: 2.1 MB Download

Cite the Following Article

DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
Soumitra Guin, Raman Gupta, Debashis Majee and Sampak Samanta
Beilstein J. Org. Chem. 2018, 14, 2771–2778. https://doi.org/10.3762/bjoc.14.254

How to Cite

Guin, S.; Gupta, R.; Majee, D.; Samanta, S. Beilstein J. Org. Chem. 2018, 14, 2771–2778. doi:10.3762/bjoc.14.254

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: 187.6 KB Download

Citations to This Article

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

Scholarly Works

  • Patel, A. K.; Samanta, S. Organocatalyzed Double C(sp3)−H Alkylation of Cyclic N‐Sulfonyl Ketimines with 3‐Chloropropiophenones: Selective Access to 2,3,6‐Trisubstituted Pyridines. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300631
  • Wang, S.; Li, Y.; Zhang, Z.; Xiang, J.; Zheng, L. Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita-Baylis-Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines. The Journal of organic chemistry 2023, 88, 3636–3649. doi:10.1021/acs.joc.2c02843
  • Lodhi, R.; Patel, A. K.; Samanta, S. AgOTf/Et3N Cooperative Catalysis Enabled One‐Pot Access to α‐(Indolizinylethyl)‐Substituted N‐Sulfonyl Ketimines via an Imino‐Alkyne Cyclization. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202200569
  • Patel, A. K.; Rathor, S. S.; Samanta, S. Regioselective access to di- and trisubstituted pyridines via a metal-oxidant-solvent-free domino reaction involving 3-chloropropiophenones. Organic & biomolecular chemistry 2022, 20, 6759–6765. doi:10.1039/d2ob01193j
  • Goud, S. B.; Guin, S.; Prakash, M.; Samanta, S. Cu(OAc)2/DABCO-mediated domino reaction of vinyl malononitriles with cyclic sulfamidate imines: access to 6-hydroxyaryl-2-aminonicotinonitriles. Organic & biomolecular chemistry 2022, 20, 352–357. doi:10.1039/d1ob02095a
  • Guin, S.; Majee, D.; Samanta, S. Unmasking the reverse reactivity of cyclic N-sulfonyl ketimines: multifaceted applications in organic synthesis. Chemical communications (Cambridge, England) 2021, 57, 9010–9028. doi:10.1039/d1cc03439a
  • Khassenova, G.; Mancheño, O. G. Lewis Base-Brønsted Acid Co-catalyzed Morita-Baylis-Hillman Reaction of Cyclic Sulfamidate Imines. European Journal of Organic Chemistry 2021, 2021, 2752–2755. doi:10.1002/ejoc.202100345
  • Prakash, M.; Lodhi, R.; Samanta, S. Substrate-Controlled Domino Reaction of N-Sulfonyl Ketimines with 2-Aroyl-1-chlorocyclopropanecarboxylates: Access to Cyclopenta[c]chromenes and Benzo[f]cyclopenta[d][1,2]thiazepine Dioxides. The Journal of organic chemistry 2021, 86, 6721–6733. doi:10.1021/acs.joc.1c00459
  • Gujjarappa, R.; Vodnala, N.; Malakar, C. C. Recent Advances in Pyridine-Based Organocatalysis and its Application towards Valuable Chemical Transformations. ChemistrySelect 2020, 5, 8745–8758. doi:10.1002/slct.202002765
  • Arupula, S. K.; Qureshi, A. A.; Swamy, K. C. K. Lewis Base-Switched [3 + 3] and [4 + 2] Annulation Reactions of δ-Acetoxy Allenoates with Cyclic N-Sulfonyl Imines: Divergent Synthesis of Functionalized α-Pyridyl Acetates and Teraryl Scaffolds. The Journal of organic chemistry 2020, 85, 4130–4144. doi:10.1021/acs.joc.9b03281
  • Kazemi, M. Based on MFe2O4 (M=Co, Cu, and Ni): Magnetically recoverable nanocatalysts in synthesis of heterocyclic structural scaffolds. Synthetic Communications 2020, 50, 1899–1935. doi:10.1080/00397911.2020.1723109
  • Guin, S.; Gudimella, S. K.; Samanta, S. 1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines. Organic & biomolecular chemistry 2020, 18, 1337–1342. doi:10.1039/c9ob02708d
  • Prakash, M.; Gudimella, S. K.; Lodhi, R.; Guin, S.; Samanta, S. NH4OAc-Promoted Domino Route to Hydroxyarylated Unsymmetrical Pyridines under Neat Conditions. The Journal of organic chemistry 2020, 85, 2151–2167. doi:10.1021/acs.joc.9b02896
  • Ahuja, M.; Majee, D.; Sharma, P.; Kumar, A.; Mobin, M.; Samanta, S. Metal‐Free Based Domino Approach to Pyrano‐Fused‐Pyrido[3,2,1‐jk]carbazolones: Antibacterial and Molecular Docking Studies. ChemistrySelect 2019, 4, 9096–9101. doi:10.1002/slct.201902149
  • Arupula, S. K.; Gudimella, S. K.; Guin, S.; Mobin, M.; Samanta, S. Chemoselective cyclization of N-sulfonyl ketimines with ethenesulfonyl fluorides: access to trans-cyclopropanes and fused-dihydropyrroles. Organic & biomolecular chemistry 2019, 17, 3451–3461. doi:10.1039/c9ob00433e
Other Beilstein-Institut Open Science Activities