biostudies-literatureDzedulionyte KInternal Grant Agency of Palacký UniversityLietuvos Mokslo Taryba8666https://www.ebi.ac.uk/biostudies/studies/S-EPMC9783606biostudies-literatureUnknown27(24)A general approach towards the synthesis of tetrahydro-4<i>H</i>-pyrazolo[1,5-<i>a</i>][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-<i>a</i>]indol-1-one and tetrahydro-1<i>H</i>-benzo[4,5]imidazo[1,2-<i>a</i>][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1<i>H</i>-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1<i>H</i>-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation-yielding target pyrazolo[1,5-<i>a</i>][1,4]diazepin-4-ones. A straightforward two-step synthetic approach was applied to expand the current study and successfully functionalize ethyl 1<i>H</i>-indole- and ethyl 1<i>H</i>-benMolecules (Basel, Switzerland)Convenient Synthesis of <i>N</i>-Heterocycle-Fused Tetrahydro-1,4-diazepinones.PMC9783606No. S-MIP-20-60IGA_PrF_2022_012Dzedulionyte KMoravek VVeiksaite MRackauskiene GSackus AArbaciauskiene EMalinauskiene VZukauskaite AfalseConvenient Synthesis of <i>N</i>-Heterocycle-Fused Tetrahydro-1,4-diazepinones.A general approach towards the synthesis of tetrahydro-4<i>H</i>-pyrazolo[1,5-<i>a</i>][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-<i>a</i>]indol-1-one and tetrahydro-1<i>H</i>-benzo[4,5]imidazo[1,2-<i>a</i>][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1<i>H</i>-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1<i>H</i>-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation-yielding target pyrazolo[1,5-<i>a</i>][1,4]diazepin-4-ones. A straightforward two-step synthetic approach was applied to expand the current study and successfully functionalize ethyl 1<i>H</i>-indole- and ethyl 1<i>H</i>-ben2022-01-01T00:00:00Z2022 Dec2025-04-05T15:42:34.947Z2025-04-05T15:42:34.947ZS-EPMC97836063655780010.3390/molecules27248666