Dark Mode Light Mode

Keep Up to Date with the Most Important News

By pressing the Subscribe button, you confirm that you have read and are agreeing to our Privacy Policy and Terms of Use
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.
Join us on a journey where chemistry meets creativity, and the wonders of science unfold. Quench your intellectual thirst with thought-provoking articles that transcend the boundaries of conventional knowledge.

Synthesis of pyrroles from isoxazoles by an O-to-C skeletal edit

Synthesis of pyrroles from isoxazoles by an O-to-C skeletal edit Synthesis of pyrroles from isoxazoles by an O-to-C skeletal edit


  • Pandhurnekar, C. P., Pandhurnekar, H. C., Mungole, A. J., Butoliya, S. S. & Yadao, B. G. A review of recent synthetic strategies and biological activities of isoxazole. J. Heterocycl. Chem. 60, 537–565 (2023).

    Article 
    CAS 

    Google Scholar
     

  • Ganesh, B. H. et al. Pyrrole: a decisive scaffold for the development of therapeutic agents and structure–activity relationship. ChemMedChem. 19, e202300447 (2024).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Martis, G. J. & Gaonkar, S. L. Advances in isoxazole chemistry and their role in drug discovery. RSC Adv. 15, 8213–8243 (2025).

    Article 
    ADS 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Joule, J. A. & Mills, K. Heterocyclic Chemistry 5th edn (Wiley-Blackwell, 2010).

  • Puriņš, M., Elgindy, C. & Levin, M. D. Shape-conserving atom replacements. Chem. Rev. https://doi.org/10.1021/acs.chemrev.5c01009 (2026).

    Article 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Cheng, G., Lv, W. & Xue, L. Base-promoted ring-closing carbonyl–allene metathesis for the synthesis of 2,4-disubstituted pyrroles. Green Chem. 20, 4414–4417 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Newman-Stonebraker, S. H. et al. Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis. Science 374, 301–308 (2021).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar
     

  • Pearson, T. J. et al. Aromatic nitrogen scanning by ipso-selective nitrene internalization. Science 381, 1474–1479 (2023).

    Article 
    ADS 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Puriņš, M., Nakahara, H. & Levin, M. D. Bridging the pyridine-pyridazine synthesis gap by skeletal editing. Science 389, 295–298 (2025).

    Article 
    ADS 
    PubMed 

    Google Scholar
     

  • Wang, Z., Xu, P., Guo, S.-M., Daniliuc, C. G. & Studer, A. C-to-N atom swapping and skeletal editing in indoles and benzofurans. Nature 642, 92–98 (2025).

    Article 
    ADS 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Choi, W., Jang, A. & Hong, S. Pyridine-to-pyridazine skeletal editing. J. Am. Chem. Soc. 147, 42042–42050 (2025).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar
     

  • Paschke, A.-S. K., Schiele, S., Pinard, C., Sandrini, F. & Morandi, B. Chemodivergent C-to-N atom swap from benzofurans to benzisoxazoles and benzoxazoles. Chem. Sci. 16, 11464–11467 (2025).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Conboy, A. & Greaney, M. F. Synthesis of benzenes from pyridines via N to C switch. Chem. 10, 1940–1949 (2024).

    Article 
    CAS 

    Google Scholar
     

  • Falcone, N. A., He, S., Hoskin, J. F., Mangat, S. & Sorensen, E. J. N-Oxide-to-carbon transmutations of azaarene N-oxides. Org. Lett. 26, 4280–4285 (2024).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Kim, D. et al. Photocatalytic furan-to-pyrrole conversion. Science 386, 99–105 (2024).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar
     

  • Akram, T., Niu, C., Qiu, W.-J. & Wang, G.-W. An O-to-N swapping reaction via triflic anhydride-mediated lactamization of 3,3-diarylbenzofuranones with nitriles. Adv. Synth. Catal. 368, e70230 (2026).

    Article 
    CAS 

    Google Scholar
     

  • Zhang, Y.-Q., Li, S.-H., Zhang, X. & Koh, M. J. Photocatalytic oxygen-atom transmutation of oxetanes. Nature 647, 906–912 (2025).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar
     

  • Bartholomew, G. L. et al. Cheminformatic analysis of core-atom transformations in pharmaceutically relevant heteroaromatics. J. Med. Chem. 68, 6027–6040 (2025).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Albright, H. et al. Carbonyl–olefin metathesis. Chem. Rev. 121, 9359–9406 (2021).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Taishev, A. E., Galenko, E. E., Novikov, M. S. & Khlebnikov, A. F. Azirine-based synthesis of alkynylpyrroles. J. Org. Chem. 91, 767–779 (2026).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Malcor, J.-D. et al. Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones. Tetrahedron 70, 4631–4639 (2014).

    Article 
    CAS 

    Google Scholar
     

  • Rostovskii, N. V. et al. Switchable synthesis of pyrroles and pyrazines via Rh(II)-catalyzed reaction of 1,2,3-triazoles with isoxazoles: experimental and DFT evidence for the 1,4-diazahexatriene intermediate. J. Org. Chem. 82, 256–268 (2017).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Agafonova, A. V., Funt, L. D., Novikov, M. S. & Khlebnikov, A. F. An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates—versatile building blocks for assembling pyrrolo-fused heterocycles. Org. Biomol. Chem. 19, 1976–1984 (2021).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Lei, X., Li, L., He, Y.-P. & Tang, Y. Rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles: entry to polysubstituted 3-aminopyrroles. Org. Lett. 17, 5224–5227 (2015).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar
     

  • Baltazzi, E. & Krimen, L. I. Recent advances in the chemistry of pyrrole. Chem. Rev. 63, 511–556 (1963).

    Article 
    CAS 

    Google Scholar
     

  • van Leusen, A. M., Siderius, H., Hoogenboom, B. E. & van Leusen, D. A new and simple synthesis of the pyrrole ring system from michael acceptors and tosylmethylisocyanides. Tetrahedron Lett. 13, 5337–5340 (1972).

    Article 

    Google Scholar
     

  • Shi, T. et al. Recent advances in the syntheses of pyrroles. Green Synth. Catal. 4, 20–34 (2023).

    CAS 

    Google Scholar
     

  • Kanova, N., Dundar, B. A., Kelgokmen, Y. & Zora, M. One-pot synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones via intermediacy of 1,4-oxazepines. J. Org. Chem. 86, 6289–6304 (2021).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Cacchi, S., Fabrizi, G. & Filisti, E. N-propargylic β-enaminones: common intermediates for the synthesis of polysubstituted pyrroles and pyridines. Org. Lett. 10, 2629–2632 (2008).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Martins, M. A. P. et al. Intramolecular cyclization of N-propargylic β-enaminones catalyzed by silver. Tetrahedron Lett. 54, 847–849 (2013).

    Article 
    CAS 

    Google Scholar
     

  • Burton, A. G., Forsythe, P. P., Johnson, C. D. & Katritzky, A. R. The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XXVII. The nitration and hydrogen exchange of 1,3,5-trimethylpyrazole, 3,5-dimethylisoxazole, and 3,5-dimethylisothiazole. J. Chem. Soc. B 6, 2365–2371 (1971).

  • Woodward, R. B. & Olofson, R. A. The reaction of isoxazolium salts with bases. J. Am. Chem. Soc. 83, 1007–1009 (1961).

    Article 
    ADS 
    CAS 

    Google Scholar
     

  • Kashima, C. et al. The ring cleavage of 3,5-disubstituted isoxazolium salts with alkoxides. Heterocycles 7, 241–241 (1977).

    Article 
    CAS 

    Google Scholar
     

  • Ikeda, R. & Kuwano, R. Asymmetric hydrogenation of isoxazolium triflates with a chiral iridium catalyst. Chem. Eur. J. 22, 8610–8618 (2016).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • González-Nogal, A. M. & Calle, M. Silylated azolium salts and their applications in the synthesis of azolines and β-enaminoketones bearing allyl-, vinyl-, and acylsilane or α-silylketone units. Tetrahedron 65, 5472–5483 (2009).

    Article 

    Google Scholar
     

  • Albertola, A., Antolín, L. F., González, A., Laguna, M. A. & Pulido, F. J. Reaction of isoxazoles and isoxazolium salts with organometallic reagents. Synthesis of dihydroisoxazoles. J. Chem. Soc. Perkin Trans. 1 17, 791–794 (1988).

  • Nitta, M. & Kobayashi, T. Reductive ring opening of isoxazoles with Mo(CO)6 and water. J. Chem. Soc. Chem. Commun. 18, 877–878 (1982).

  • Wenkert, E. & Han, A. Nickel-catalyzed reactions of thiazoles, isoxazoles, oxazolines and thiazolines with grignard reagents. Heterocycles 30, 929 (1990).

    Article 
    CAS 

    Google Scholar
     

  • Singh, M., Singh, S., Gupta, N., Singh, A. & Singh, M. S. Carbonyl–allene metathesis of S-allenyl-α-oxo-S,S/N,S-ketene acetals: a thermally driven intramolecular tandem [2 + 2] cycloaddition–retro-cyclization. Org. Lett. 28, 1355–1360 (2026).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Wagner, A. M. & Sanford, M. S. Palladium-catalyzed C−H arylation of 2,5-substituted pyrroles. Org. Lett. 13, 288–291 (2011).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Lanzilotti, A. E., Littell, R., Fanshawe, W. J., McKenzie, T. C. & Lovell, F. M. Stereoselective reduction of some indoles with triethylsilane-trifluoroacetic Acid. J. Org. Chem. 44, 4809–4813 (1979).

    Article 
    CAS 

    Google Scholar
     

  • Ji, P. et al. Single-site cobalt catalysts at new Zr82-O)82-OH)4 metal-organic framework nodes for highly active hydrogenation of alkenes, imines, carbonyls, and heterocycles. J. Am. Chem. Soc. 138, 12234–12242 (2016).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar
     

  • Doak, K. W. & Corwin, A. H. Kinetics of pyrrole substitutions. The iodination reaction. J. Am. Chem. Soc. 71, 159–163 (1949).

    Article 
    ADS 
    CAS 

    Google Scholar
     

  • Shirley, D. A., Gross, B. H. & Roussel, P. A. Metalation of pyrrole, 1-methylpyrrole, and 1-phenylpyrrole with n-butyllithium. J. Org. Chem. 20, 225–231 (1955).

    Article 
    CAS 

    Google Scholar
     

  • Karadeniz, E. & Zora, M. Synthesis of 1-azaspiro[4.5]deca-1,3-dienes from N-propargylic β-enaminones in basic medium. Synthesis 51, 2157–2170 (2019).

    Article 
    CAS 

    Google Scholar
     

  • Ge, B., Lv, W., Yu, J., Xiao, S. & Cheng, G. Base-promoted C–C bond cleavage for the synthesis of 2,3,4-trisubstituted pyrroles from N-propargyl β-enaminones. Org. Chem. Front. 5, 3103–3107 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Yamauchi, T. et al. Transition metal-free cyclization of N-Boc-N-propargylenamines. Heterocycles 100, 719 (2020).

    Article 

    Google Scholar
     

  • Yadav, V. K. in Steric and Stereoelectronic Effects in Organic Chemistry (ed. Yadav, V. K.) 107–128 (Springer, 2021).

  • Malhotra, S. K., Moakley, D. F. & Johnson, F. Steric interference in allylic and pseudo-allylic systems: A(1,2) strain between methyl group and hydrogen. Chem. Commun. 3, 448–449 (1967).



  • Source link

    Keep Up to Date with the Most Important News

    By pressing the Subscribe button, you confirm that you have read and are agreeing to our Privacy Policy and Terms of Use
    Add a comment Add a comment

    Leave a Reply

    Your email address will not be published. Required fields are marked *

    Previous Post
    Multiyear tropical warm pool warming drives slowdown in Antarctic mass loss

    Multiyear tropical warm pool warming drives slowdown in Antarctic mass loss

    Next Post
    A biased allosteric modulator is a molecular glue for β2AR dimerization

    A biased allosteric modulator is a molecular glue for β2AR dimerization

    Advertisement