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 Zr8(μ2-O)8(μ2-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).