| Title |
Convenient synthesis of N-heterocycle-fused tetrahydro-1,4-diazepinones / |
| Authors |
Dzedulionytė, Karolina ; Veikšaitė, Melita ; Morávek, Vít ; Malinauskienė, Vida ; Račkauskienė, Greta ; Šačkus, Algirdas ; Žukauskaitė, Asta ; Arbačiauskienė, Eglė |
| DOI |
10.3390/molecules27248666 |
| Full Text |
|
| Is Part of |
Molecules.. Basel : MDPI. 2022, vol. 27, iss. 24, art. no. 8666, p. 1-28.. ISSN 1420-3049 |
| Keywords [eng] |
pyrazole ; indole ; benzimidazole ; fused N-heterocycles ; regioselective N-alkylation ; oxirane ring-opening ; cyclisation |
| Abstract [eng] |
A general approach towards the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-a]indol-1-one and tetrahydro-1H-benzo[4,5]imidazo[1,2-a][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1H-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation—yielding target pyrazolo[1,5-a][1,4]diazepin-4-ones. A straightforward two-step synthetic approach was applied to expand the current study and successfully functionalize ethyl 1H-indole- and ethyl 1H-benzo[d]imidazole-2-carboxylates. The structures of fused heterocyclic compounds were confirmed by 1H, 13C, and 15N-NMR spectroscopy and HRMS investigation. |
| Published |
Basel : MDPI |
| Type |
Journal article |
| Language |
English |
| Publication date |
2022 |
| CC license |
|
