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Facile Synthesis of Polyisothioureas via Alternating Copolymerization of aziridines and Isothiocayanates

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Chinese Journal of Polymer Science 2024年第3期42卷 292-298,I0005页

作者： Hao-Tian Zhang Ming-Xin Niu Qi Zhang Chen-Yang Hu Xuan Pang Key Laboratory of Polymer Ecomaterials Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China Department of Materials Science and Engineering Jilin UniversityChangchun 130025China School of Applied Chemistry and Engineering University of Science and Technology of ChinaHefei 230026China

Isothiourea is an important class of sulfur-containing molecules showing unique catalytic and biological activities. As such,polyisothiourea is envisioned to be an interesting type of polymer that potentially exhibits a number of interesting properties. However, there is no access to synthesizing well-defined polyisothiourea, and currently isothiourea-containing polymers are mainly prepared by immobilizing onto other polymer's side chain. Herein, we report the first facile synthesis of polyisothioureas via alternating copolymerization of aziridines and isothiocayanates. Mediated by the catalytic system of phosphazene superbases/alcohol, a broad scope of aziridines and isothiocayanates could be transformed into polyisothioureas with adjustable substitutions(11 examples). The structures of obtained polyisothioureas were fully characterized with ^(1)H-NMR, ^(13)C-NMR, and ^(1)H-^(13)C HMBC NMR. Moreover, the polyisothioureas show tunable thermal properties depending on substitutions on the isothiourea linkages. The novel structure of these polyisothioureas will enable a powerful platform for the discovery of nextgeneration functional plastics.

关键词： Polyisothioureas Alternative copolymer aziridines Isothiocayanates

Ring Opening of N-Sulfonyl aziridines by Amines in Silica-Water

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Chinese Journal of Chemistry 2014年第11期32卷 1135-1142页

作者： Tiantian Li Xiaosi Ma Junmei Qi Feifei Sun Ning Ma Department of Chemistry School of ScienceTianjin UniversityTianjin 300072China Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Tianjin 300072China

Ring opening reactions of N-sulfonyl aziridines by primary and secondary amines in silica gel(SG)-water system were achieved,which provided a mild,practical and environmentally benign method to synthesize mono-and bis-sulfonyl substituted *** primary and secondary amines were used in excess,they reacted with N-sulfonyl aziridines smoothly at room temperature,mainly affording 1∶1 ring opening *** of primary amines with 2 *** aziridines produced 2∶1 ring opening *** 1∶1 products can be cyclized with CS2 to synthesize N-sulfonyl cyclothioureas also in water.

关键词： aziridines ring opening amines silica gel reactions in water

Oxidative Dehydrogenative [3+3] Annulation of Benzylhydrazines with aziridines Leading to Tetrahydrotriazines

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Chinese Journal of Chemistry 2019年第9期37卷 878-882页

作者： Haitao Li Jia Liang Congde Huo Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of EducationCollege of Chemistry and Chemical EngineeringNorthwest Normal UniversityLanzhouGansu 730070China

Oxidative dehydrogenative [3+3] annulation of benzylhydrazines with N-sulfonylaziridines is described.A series of complex tetrahydro-1,2,4-triazines were produced under mild reaction conditions.

关键词： Benzylhydrazines aziridines Leading Tetrahydrotriazines

Tri-n-butylphosphane catalyzed ring opening of aziridines with secondary amines

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Chinese Chemical Letters 2012年第6期23卷 657-660页

作者： Wan Xuan Zhang Li Su Wei Gang Hu Jie Zhou Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules Hubei University Wuhan 430062 China

Ring opening of aziridine with dialkyl amine took place readily in the presence of catalytic amounts of tri-n-butylphosphane （10 mol%） in the mixture of CH3CN/H20 （10：1）, giving corresponding vicinal diamines in mediate to high yields （58-95%） with good regioselectivitie, while aromatic secondary amine could not react under the same conditions. Tri-n-butylphosphane exhibited different catalytic selectivity to amines from Lewis acid catalysts.

关键词： aziridines Ring-opening reaction Secondary amine Tfi-n-butylphosphane Vicinal diamine

Synthesis of Substituted Aziridine from (1S,2S)-2-Amino-1- (4-Nitrophenyl)- 1,3-Propanediol

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Wuhan University Journal of Natural Sciences 2000年第3期5卷 345-347页

作者： Yang Shao-rong Hu Xian-ming Liu Jun Shu Jia-you Feng Dai-jun Huang Jin-xia College of Chemistry and Environmental Science Wuhan University Wuhan China College of Chemistry Hubei University Wuhan China

(2S, 3R)-2-acetooxymethanyl-3-(P-nitrophenyl)-N-tosylaziridine 5 was synthesized from (1S, 2S)-2-amino-1-(4-nitrophenyl)-1, 3-propanediol 1 in four steps with a 24.8% overall yield. This reaction is stereospecific and occurs an expectable configuration inversion at α-carbon atom of benzyl group. The structure of substituted aziridine was determined on FT-IR, NMR, MS and so on.

关键词： aziridines synthesis chloramphenicol