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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 Jean-Daniel Malcor 1be63bfe4134ebd4f44a83bdf25d0efb ibcp.fr jean-daniel-malcor 1186916 719360-1186916 https://orcid.org/0000-0003-4208-1294 Yann Brouillette 225400-0 Julien Graffion 594455-0 Kim Spielmann 1178468-0 Nicolas Masurier 4875547391631510649479d14fc54791 umontpellier.fr nmasurier 1086355 547511-1086355 https://orcid.org/0000-0001-9169-8149 https://www.idref.fr/07356902X Ludovic Maillard 7251175e71fc53f942f017644573a86a umontpellier.fr ludovic-t-maillard 767790 688231-767790 https://orcid.org/0000-0002-9437-9765 https://www.idref.fr/103785973 Jean Martinez 133961-0 Vincent Lisowski 6e0b660f8d21fd940ecd1c913404f1bc umontpellier.fr 1096014 188855-1096014 https://orcid.org/0000-0002-4474-4242 https://www.idref.fr/081276222 Anthony Herrada fcb22fb3703cf470da2926a2fd72f58a unimes.fr 2022-02-09 16:56:34 2024-06-12 17:38:20 2022-02-09 16:56:34 2014-08 contributor Anthony Herrada fcb22fb3703cf470da2926a2fd72f58a unimes.fr CCSD hal-03563449 https://hal.umontpellier.fr/hal-03563449 malcor:hal-03563449 <i>Tetrahedron</i>, 2014, 70 (31), pp.4631-4639. <a target="_blank" href="https://dx.doi.org/10.1016/j.tet.2014.05.046">⟨10.1016/j.tet.2014.05.046⟩</a> Tetrahedron, 2014, 70 (31), pp.4631-4639. ⟨10.1016/j.tet.2014.05.046⟩ CNRS - Centre national de la recherche scientifique Ecole Nationale Supérieure de Chimie de Montpellier Institut des Biomolécules Max Mousseron Institut de Chimie du CNRS Chimie Université de Montpellier Université de Montpellier (2015-2021) International No Yes 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 Jean-Daniel Malcor 1be63bfe4134ebd4f44a83bdf25d0efb ibcp.fr jean-daniel-malcor 1186916 719360-1186916 https://orcid.org/0000-0003-4208-1294 Yann Brouillette 225400-0 Julien Graffion 594455-0 Kim Spielmann 1178468-0 Nicolas Masurier 4875547391631510649479d14fc54791 umontpellier.fr nmasurier 1086355 547511-1086355 https://orcid.org/0000-0001-9169-8149 https://www.idref.fr/07356902X Ludovic Maillard 7251175e71fc53f942f017644573a86a umontpellier.fr ludovic-t-maillard 767790 688231-767790 https://orcid.org/0000-0002-9437-9765 https://www.idref.fr/103785973 Jean Martinez 133961-0 Vincent Lisowski 6e0b660f8d21fd940ecd1c913404f1bc umontpellier.fr 1096014 188855-1096014 https://orcid.org/0000-0002-4474-4242 https://www.idref.fr/081276222 19385 0040-4020 Tetrahedron Elsevier 70 31 4631-4639 2014-08 10.1016/j.tet.2014.05.046 English Chemical Sciences Journal articles Journal articles Journal articles

A convenient synthesis of pyrrolo[3,2-d][1,3]oxazine-2,4-dione 4 is described and its reactivity towards various nucleophiles studied. The regioselective ring opening of anhydride 4 or its N-alkylated analog 25 in the presence of alanine or proline afforded, respectively, imidazolidinedione 22 and N-protected pyrrolo[3,2-e][1,4]diazepines 30 and 31 in a one-pot process. In a last part of this study, an alternative route to produce a library of eight non protected pyrrolo[3,2-e][1,4]diazepine-2,5-diones 35a–h is described to overcome the limited reactivity of anhydride 4.

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