Improved synthetic methodology, substrate scope and X-ray crystal structure for N, N’-disubstituted guanidines

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Improved synthetic methodology, substrate scope and X-ray crystal structure for N, N’-disubstituted guanidines

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Improved synthetic methodology, substrate scope and X-ray crystal structure for N, N’-disubstituted guanidines

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

<a href="/cs/project/LM2023051" target="_blank" >LM2023051: Výzkumná infrastruktura CzechNanoLab</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ChemistrySelect

ISSN

2365-6549

e-ISSN

2365-6549

Svazek periodika

9

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

8

Strana od-do

e202304381

Kód UT WoS článku

001140044400001

EID výsledku v databázi Scopus

2-s2.0-85181958417