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Article

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

by
Emilis Gudelis
1,2,
Sonata Krikštolaitytė
2,
Monika Stančiauskaitė
2,
Urtė Šachlevičiūtė
1,
Aurimas Bieliauskas
1,
Vaida Milišiūnaitė
1,
Rokas Jankauskas
1,
Neringa Kleizienė
1,
Frank A. Sløk
3 and
Algirdas Šačkus
1,2,*
1
Institute of Synthetic Chemistry, Kaunas University of Technology, K. Baršausko g. 59, LT-51423 Kaunas, Lithuania
2
Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania
3
Vipergen ApS, Gammel Kongevej 23A, V DK-1610 Copenhagen, Denmark
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(3), 1091; https://doi.org/10.3390/molecules28031091
Submission received: 16 December 2022 / Revised: 11 January 2023 / Accepted: 17 January 2023 / Published: 21 January 2023
(This article belongs to the Special Issue Recent Advances in Heterocycles Synthesis)
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Abstract

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.
Keywords: azetidine; oxetane; heterocyclic amines; heterocyclic amino acids; aza-Michael addition; Suzuki–Miyaura cross-coupling reaction azetidine; oxetane; heterocyclic amines; heterocyclic amino acids; aza-Michael addition; Suzuki–Miyaura cross-coupling reaction
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MDPI and ACS Style

Gudelis, E.; Krikštolaitytė, S.; Stančiauskaitė, M.; Šachlevičiūtė, U.; Bieliauskas, A.; Milišiūnaitė, V.; Jankauskas, R.; Kleizienė, N.; Sløk, F.A.; Šačkus, A. 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. Molecules 2023, 28, 1091. https://doi.org/10.3390/molecules28031091

AMA Style

Gudelis E, Krikštolaitytė S, Stančiauskaitė M, Šachlevičiūtė U, Bieliauskas A, Milišiūnaitė V, Jankauskas R, Kleizienė N, Sløk FA, Šačkus A. 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. Molecules. 2023; 28(3):1091. https://doi.org/10.3390/molecules28031091

Chicago/Turabian Style

Gudelis, Emilis, Sonata Krikštolaitytė, Monika Stančiauskaitė, Urtė Šachlevičiūtė, Aurimas Bieliauskas, Vaida Milišiūnaitė, Rokas Jankauskas, Neringa Kleizienė, Frank A. Sløk, and Algirdas Šačkus. 2023. "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" Molecules 28, no. 3: 1091. https://doi.org/10.3390/molecules28031091

APA Style

Gudelis, E., Krikštolaitytė, S., Stančiauskaitė, M., Šachlevičiūtė, U., Bieliauskas, A., Milišiūnaitė, V., Jankauskas, R., Kleizienė, N., Sløk, F. A., & Šačkus, A. (2023). 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. Molecules, 28(3), 1091. https://doi.org/10.3390/molecules28031091

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