Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2018 Feb 23;8(16):8450-8454.
doi: 10.1039/c8ra00524a.

Iridium-catalysed direct sulfamidation of quinazolinones

Yadong Feng  1 , Yudong Li  1 , Yunliang Yu  1 , Lianhui Wang  1 , Xiuling Cui  1
Affiliations

Iridium-catalysed direct sulfamidation of quinazolinones

Yadong Feng et al. RSC Adv. .

Abstract

Ir-catalysed direct sulfamidation of quinazolinones has been achieved. A series of ortho-diamided quinazolinones were obtained in up to 96% yields. This transformation could proceed smoothly with a low catalyst loading under mild conditions with nitrogen released as the sole byproduct. This approach potentially provides an environmentally benign sulfamidation process for atom/step economic syntheses of useful pharmaceutical molecules or important building blocks.

PubMed Disclaimer

Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Ir-catalysed direct amidation of 2-arylquinazolinones.
Scheme 2
Scheme 2. Exploration of the reaction mechanism.
Scheme 3
Scheme 3. The proposed reaction mechanism.
See this image and copyright information in PMC

Similar articles

See all similar articles

References

    1. For selected reviews see:

    2. Doyle M. P. Goldberg K. I. Acc. Chem. Res. 2012;45:777. doi: 10.1021/ar300096z. - DOI - PubMed
    3. Bruckl T. Baxter R. D. Ishihara Y. Baran P. S. Acc. Chem. Res. 2012;45:826. doi: 10.1021/ar200194b. - DOI - PMC - PubMed
    4. Arockiam P. B. Bruneau C. Dixneuf P. H. Chem. Rev. 2012;112:5879. doi: 10.1021/cr300153j. - DOI - PubMed
    5. Sun C.-L. Li B.-J. Shi Z.-J. Chem. Rev. 2011;111:1293. doi: 10.1021/cr100198w. - DOI - PubMed
    6. Lyons T. W. Sanford M. S. Chem. Rev. 2010;110:1147. doi: 10.1021/cr900184e. - DOI - PMC - PubMed
    7. Yamaguchi J. Yamaguchi A. D. Itami K. Angew. Chem., Int. Ed. 2012;51:8960. doi: 10.1002/anie.201201666. - DOI - PubMed
    8. Colby D. A. Bergman R. G. Ellman J. A. Chem. Rev. 2010;110:624. doi: 10.1021/cr900005n. - DOI - PMC - PubMed
    9. Wencel-Delord J. Drcge T. Liu F. Glorius F. Chem. Soc. Rev. 2011;40:4740. doi: 10.1039/C1CS15083A. - DOI - PubMed
    10. Satoh T. Miua M. Chem.–Eur. J. 2010;16:11212. doi: 10.1002/chem.201001363. - DOI - PubMed
    11. Song G. Y. Wang F. Li X. Chem. Soc. Rev. 2012;41:3651. doi: 10.1039/C2CS15281A. - DOI - PubMed
    12. Ackermann L. Pospech J. Org. Lett. 2011;13:4153. doi: 10.1021/ol201563r. - DOI - PubMed
    13. Ueyama T. Mochida S. Fukutani T. Hirano K. Satoh T. Miura M. Org. Lett. 2011;13:706. doi: 10.1021/ol102942w. - DOI - PubMed
    14. Weissman H. Song X. Milstein D. J. Am. Chem. Soc. 2001;123:337. doi: 10.1021/ja003361n. - DOI - PubMed
    15. Wu J. Cui X. Mi X. Li Y. Wu Y. Chem. Commun. 2010;46:6771. doi: 10.1039/C0CC01448F. - DOI - PubMed
    16. Ackermann L. Wang L. Lygin A. V. Chem. Sci. 2012;3:177. doi: 10.1039/C1SC00619C. - DOI
    1. Yang W. Wang J. Wei Z. Zhang Q. Xu X. J. Org. Chem. 2016;81:1675. doi: 10.1021/acs.joc.5b02903. - DOI - PubMed
    2. Walker S. E. Jordan-Hore J. A. Johnson D. G. Macgregor S. A. Lee A. L. Angew. Chem., Int. Ed. 2014;53:13876. doi: 10.1002/anie.201408054. - DOI - PMC - PubMed
    3. Honraedt A. Le Callonnec F. Le Grognec E. Fernandez V. Felpin F.-X. J. Org. Chem. 2013;78:4604. doi: 10.1021/jo4004426. - DOI - PubMed
    4. Zhou T. Li L. Li B. Song H. Wang B. Org. Lett. 2015;17:4204. doi: 10.1021/acs.orglett.5b01974. - DOI - PubMed
    5. Fujiwara Y. Domingo V. Seiple I. B. Gianatassio R. Del Bel M. D. Baran P. S. J. Am. Chem. Soc. 2011;133:3292. doi: 10.1021/ja111152z. - DOI - PMC - PubMed
    6. Shaaban S. Jolit A. Petkova D. Maulide N. Chem. Commun. 2015;51:13902. doi: 10.1039/C5CC03580E. - DOI - PubMed
    7. Jardim G. A. Bower J. F. Da S. J. E. Org. Lett. 2016;18:4454. doi: 10.1021/acs.orglett.6b01586. - DOI - PubMed
    8. Li B.-J. Shi Z.-J. Chem. Soc. Rev. 2012;41:5588. doi: 10.1039/C2CS35096C. - DOI - PubMed
    9. Kuhl N. Schroder N. Glorius F. Adv. Synth. Catal. 2014;356:1443. doi: 10.1002/adsc.201400197. - DOI
    10. Mo J. Wang L. Liu Y. Cui X. Synthesis. 2015;47:439. doi: 10.1055/s-0034-1379890. - DOI
    1. Ackermann L. Vicente R. Kapdi A. R. Angew. Chem., Int. Ed. 2009;48:9792. doi: 10.1002/anie.200902996. - DOI - PubMed
    2. Alberico D. Scott M. E. Lautens M. Chem. Rev. 2007;107:174. doi: 10.1021/cr0509760. - DOI - PubMed
    3. Lyons T. W. Sanford M. S. Chem. Rev. 2010;110:1147. doi: 10.1021/cr900184e. - DOI - PMC - PubMed
    4. Giri R. Shi B.-F. Engle K. M. Maugel N. Yu J.-Q. Chem. Soc. Rev. 2009;38:3242. doi: 10.1039/B816707A. - DOI - PubMed
    5. McMurray L. O'Hara F. Gaunt M. J. Chem. Soc. Rev. 2011;40:1885. doi: 10.1039/C1CS15013H. - DOI - PubMed
    6. Battiste M. A. Pelphrey P. M. Wright D. L. Chem.–Eur. J. 2006;12:3438. doi: 10.1002/chem.200501083. - DOI - PubMed
    7. Butenschön H. Angew. Chem., Int. Ed. 2008;47:5287. doi: 10.1002/anie.200801738. - DOI - PubMed
    8. Ylijoki K. E. O. Stryker J. M. Chem. Rev. 2013;113:2244. doi: 10.1021/cr300087g. - DOI - PubMed
    9. Harmata M. Chem. Commun. 2010;46:8886. doi: 10.1039/C0CC03620J. - DOI - PubMed
    1. Nanda A. K. Ganguli S. Chakraborty R. Molecules. 2007;12:2413. doi: 10.3390/12102413. - DOI - PMC - PubMed
    1. Chan J.-H. Hong J.-S. Kuyper L. F. Baccanari D. P. Joyner S. S. Tansik R. L. Boytos C. M. Rudolph S. K. J. Med. Chem. 1995;38:3608. doi: 10.1021/jm00018a021. - DOI - PubMed