| Title |
Synthesis of new azetidine and oxetane amino acid derivatives through aza-Michael addition of NH-heterocycles with methyl 2-(azetidin- or oxetan-3-ylidene)acetates / |
| Authors |
Gudelis, Emilis ; Krikštolaitytė, Sonata ; Stančiauskaitė, Monika ; Šachlevičiūtė, Urtė ; Bieliauskas, Aurimas ; Milišiūnaitė, Vaida ; Jankauskas, Rokas ; Kleizienė, Neringa ; Sløk, Frank A ; Šačkus, Algirdas |
| DOI |
10.3390/molecules28031091 |
| Full Text |
|
| Is Part of |
Molecules.. Basel : MDPI. 2023, vol. 28, iss. 3, art. no. 1091, p. 1-30.. ISSN 1420-3049 |
| Keywords [eng] |
Suzuki–Miyaura cross-coupling reaction ; aza-Michael addition ; azetidine ; heterocyclic amines ; heterocyclic amino acids ; oxetane |
| Abstract [eng] |
In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (N-Boc-azetidin-3-ylidene)acetate was obtained from (N-Boc)azetidin-3-one by the DBU-catalysed Horner-Wadsworth-Emmons reaction, followed by aza-Michael addition with NH-heterocycles to yield the target functionalised 3-substituted 3-(acetoxymethyl)azetidines. Methyl 2-(oxetan-3-ylidene)acetate was obtained in a similar manner, which was further treated with various (N-Boc-cycloaminyl)amines to yield the target 3-substituted 3-(acetoxymethyl)oxetane compounds. The synthesis and diversification of novel heterocyclic amino acid derivatives were achieved through the Suzuki-Miyaura cross-coupling from the corresponding brominated pyrazole-azetidine hybrid with boronic acids. The structures of the novel heterocyclic compounds were confirmed via 1H-, 13C-, 15N-, and 19F-NMR spectroscopy, as well as HRMS investigations. |
| Published |
Basel : MDPI |
| Type |
Journal article |
| Language |
English |
| Publication date |
2023 |
| CC license |
|
