Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-diazepinones
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F22%3A73616750" target="_blank" >RIV/61989592:15310/22:73616750 - isvavai.cz</a>
Result on the web
<a href="https://www.mdpi.com/1420-3049/27/24/8666" target="_blank" >https://www.mdpi.com/1420-3049/27/24/8666</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules27248666" target="_blank" >10.3390/molecules27248666</a>
Alternative languages
Result language
angličtina
Original language name
Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-diazepinones
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10608 - Biochemistry and molecular biology
Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
MOLECULES
ISSN
1420-3049
e-ISSN
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Volume of the periodical
27
Issue of the periodical within the volume
24
Country of publishing house
CH - SWITZERLAND
Number of pages
28
Pages from-to
"8666-1"-"8666-28"
UT code for WoS article
000902698800001
EID of the result in the Scopus database
2-s2.0-85144549698