Abstract:
Intramolecular cyclization of α-bromoacyl derivatives of α-hydroxy acids affords 1,4-dioxane-2,5-diones. The method is suitable to obtain mono- and disubstituted products, the latter being formed stereoselectively as (S,S)-diastereomers, as confirmed by DFT modeling.
Citation:
B. A. Lozhkin, A. V. Shlyakhtin, V. V. Bagrov, P. V. Ivchenko, I. E. Nifant'ev, “Effective stereoselective approach to substituted 1,4-dioxane-2,5-diones as prospective substrates for ring-opening polymerization”, Mendeleev Commun., 28:1 (2018), 61–63
Linking options:
https://www.mathnet.ru/eng/mendc1664
https://www.mathnet.ru/eng/mendc/v28/i1/p61
This publication is cited in the following 21 articles:
Alexander N. Tavtorkin, Egor A. Kretov, Maria P. Ryndyk, Ilya E. Nifant'ev, Andrey V. Shlyakhtin, Vladimir V. Bagrov, Alexander A. Vinogradov, Pavel V. Ivchenko, “Synthesis, melt molding and hydrolytic degradation of poly(L-lactide-co- -methylglycolide) and its composites with carbonated apatite”, Polymer Degradation and Stability, 227 (2024), 110903
Ilya E. Nifant'ev, Alexander N. Tavtorkin, Andrey V. Shlyakhtin, Pavel V. Ivchenko, “Chemical features of the synthesis, degradation, molding and performance of poly(lactic-co-glycolic) acid (PLGA) and PLGA-based articles”, European Polymer Journal, 215 (2024), 113250
Mao Hirata, Tomoki Yoshimatsu, Shin-ichi Matsuoka, Susumu Kawauchi, Masato Suzuki, “Ring-opening polymerization of six-membered cyclic hybrid dimers composed of an oxoester and thioester”, Polym J, 56:8 (2024), 711
Wenbo Wang, Jinbo Hu, Yeqi Du, Xinyan Liu, Yanlong Liu, Ranlong Duan, Xinchao Bian, Xuesi Chen, “Ring-Opening Polymerization and Closed-Loop Recycling of 3,6-Dialkylated Morpholine-2,5-dione Monomers”, Macromolecules, 2024
Thasanaporn Ungpittagul, Arnut Virachotikul, Julien Monot, Blanca Martín‐Vaca, Didier Bourissou, “Synthesis and Organo‐Catalyzed Ring‐Opening of a Six‐Membered Heterocycle Combining Phosphonate and Ester Functions”, Adv Synth Catal, 366:4 (2024), 733
B. N. Mankaev, M. U. Agaeva, M. P. Egorov, S. S. Karlov, “Aluminum complexes based on 1,10-phenanthroline-containing diols: synthesis and application as initiators of polymerization of ε-caprolactone”, Russ Chem Bull, 71:4 (2022), 712
Pilar Sanchez-Andrada, Carmen Lopez-Leonardo, Mateo Alajarin, Comprehensive Heterocyclic Chemistry IV, 2022, 443
Evgeny D. Shaputkin, Ilya E. Nifant'ev, Vladimir V. Bagrov, Andrey V. Shlyakhtin, Dmitrii A. Abashkin, Adelya A. Galiakberova, Pavel V. Ivchenko, “Lipophilic poly(glycolide) blocks in morpholin-2-one-based CARTs for plasmid DNA delivery: Polymer regioregularity, sequence of lipophilic/polyamine blocks, and nanoparticle stability as factors of transfection efficiency”, European Polymer Journal, 181 (2022), 111644
M. V. Zabalov, B. N. Mankaev, M. P. Egorov, S. S. Karlov, “DFT study of the role of substituents in tin(II) bis(amidoethyl)amine complexes used for ε-caprolactone polymerization”, Mendeleev Commun., 32:4 (2022), 460–463
Zhaowei Jia, Jinxing Jiang, Xiaofei Zhang, Yaqin Cui, Zhichun Chen, Xiaobo Pan, Jincai Wu, “Isotactic-Alternating, Heterotactic-Alternating, and ABAA-Type Sequence-Controlled Copolyester Syntheses via Highly Stereoselective and Regioselective Ring-Opening Polymerization of Cyclic Diesters”, J. Am. Chem. Soc., 143:11 (2021), 4421
Xiaowen Xu, Jing Zhang, Tera M. Filion, Ali Akalin, Jie Song, “Modulating Mechanical and Shape-Memory Properties while Mitigating Degradation-Induced Inflammation of Polylactides by Pendant Aspirin Incorporation”, ACS Appl. Mater. Interfaces, 13:19 (2021), 22271
A. V. Shlyakhtin, I. E. Nifant'ev, M. A. Kosarev, A. N. Tavtorkin, P. V. Ivchenko, “The synthesis and copolymerization of 4-hydroxybenzylglycolide: experimental and theoretical aspects”, Mendeleev Commun., 31:5 (2021), 701–703
Ilya Nifant'ev, Pavel Komarov, Valeriya Ovchinnikova, Artem Kiselev, Mikhail Minyaev, Pavel Ivchenko, “Comparative Experimental and Theoretical Study of Mg, Al and Zn Aryloxy Complexes in Copolymerization of Cyclic Esters: The Role of the Metal Coordination in Formation of Random Copolymers”, Polymers, 12:10 (2020), 2273
Ilya E. Nifant'ev, Andrey V. Shlyakhtin, Vladimir V. Bagrov, Alexander N. Tavtorkin, Pavel D. Komarov, Andrei V. Churakov, Pavel V. Ivchenko, “Substituted glycolides from natural sources: preparation, alcoholysis and polymerization”, Polym. Chem., 11:43 (2020), 6890
Satoshi Otsugu, Yoshiharu Kimura, Hajime Nakajima, Katja Loos, “Enhancement of Tg of Poly(l‐lactide) by Incorporation of Biobased Mandelic‐Acid‐Derived Phenyl Groups by Polymerization and Polymer Blending”, Macro Chemistry & Physics, 221:3 (2020)
Adam G. Meyer, Alex C. Bissember, Christopher J.T. Hyland, Charlotte C. Williams, Monika Szabo, Melanie A. Pearsall, Isabel K. Hyland, Wesley J. Olivier, Progress in Heterocyclic Chemistry, 31, 2020, 597
B. N. Mankaev, K. V. Zaitsev, G. S. Zaitseva, A. V. Churakov, M. P. Egorov, S. S. Karlov, “Sterically hindered tetrylenes based on new 1,10-phenanthroline-containing diols: initiators for ε-caprolactone polymerization”, Russ Chem Bull, 68:2 (2019), 380
I. E. Nifant'ev, A. V. Shlyakhtin, V. V. Bagrov, P. D. Komarov, A. N. Tavtorkin, M. E. Minyaev, P. V. Ivchenko, “Efficient synthetic approach to copolymers of glycolic and lactic acids for biomedical applications”, Mendeleev Commun., 28:4 (2018), 412–414
Contact us: