Improved synthetic methodology, substrate scope and X-ray crystal structure for N, N’-disubstituted guanidines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F24%3A00616792" target="_blank" >RIV/68378271:_____/24:00616792 - isvavai.cz</a>
Result on the web
<a href="https://hdl.handle.net/11104/0363763" target="_blank" >https://hdl.handle.net/11104/0363763</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/slct.202304381" target="_blank" >10.1002/slct.202304381</a>
Alternative languages
Result language
angličtina
Original language name
Improved synthetic methodology, substrate scope and X-ray crystal structure for N, N’-disubstituted guanidines
Original language description
Guanidine is a privileged scaffold in drug discovery. Herein we report our investigations into the acid promoted amination of pyrimidine-bearing cyanamide to produce N, N’-disubstituted guanidines. Hydrochloric acid was found to be a suitable catalyst, and the substrate scope using conventional heating was investigated with 23 aniline derivatives. The highest yield was obtained with anilines having pKa in the range of 2–4. Further, a microwave synthesis was developed using 3-chloroaniline as a model substrate increasing the yield from 68 to 93%. The microwave method was especially suited for increasing yields with anilines having pKa > 3. The structure of the pyrimidine-bearing guanidines was confirmed by NMR spectroscopy, and one representative compound has been evaluated by X-ray crystallography, showing the trans-isomer as the only tautomer in solid form.
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
10302 - Condensed matter physics (including formerly solid state physics, supercond.)
Result continuities
Project
<a href="/en/project/LM2023051" target="_blank" >LM2023051: Research infrastructure CzechNanoLab</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemistrySelect
ISSN
2365-6549
e-ISSN
2365-6549
Volume of the periodical
9
Issue of the periodical within the volume
2
Country of publishing house
US - UNITED STATES
Number of pages
8
Pages from-to
e202304381
UT code for WoS article
001140044400001
EID of the result in the Scopus database
2-s2.0-85181958417