Synthesis of multifunctional 4-hydroxymethyl 2-oxazolidinones from glycidyl carbamate derivatives catalyzed by bicyclic guanidine

被引：8
作者：
Yoshida, Yoshiaki [1 ,2 ]
Endo, Takeshi [1 ]
机构：
[1] Kyushu Inst Technol, Mol Engn Inst, Tobata Ku, 1-1 Sensui Cho, Kitakyushu, Fukuoka 8048550, Japan
[2] Kyushu Inst Technol, Fac Engn, Dept Mat Sci, 1-1 Sensui Cho, Kitakyushu, Fukuoka 8048550, Japan
来源：
TETRAHEDRON LETTERS | 2021年 / 72卷
关键词：
Glycidyl carbamate; 4-Hydroxymethyl; 2-oxazolidinone; Bicyclic guanidine catalyst; Intramolecular cyclization; RING-OPENING POLYMERIZATION; OXAZOLIDINONES; ISOCYANATES; ORGANOCATALYSIS; DIISOCYANATE; REACTIVITY; EPOXIDES;
D O I：
10.1016/j.tetlet.2021.153086
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-Hydroxymethyl 2-oxazolidinones have been successfully synthesized under mild conditions by the intramolecular cyclization of glycidyl carbamate derivatives with a bicyclic guanidine as the efficient catalyst. This reaction system, which is also applicable to the multifunctional compounds, can provide bi-and tri-functional alcohols having oxazolidinone moieties. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：4
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共 41 条
[1]   Cyclic amidine hydroiodide for the synthesis of cyclic carbonates and cyclic dithiocarbonates from carbon dioxide or carbon disulfide under mild conditions [J].
Aoyagi, Naoto ;
Furusho, Yoshio ;
Endo, Takeshi .
TETRAHEDRON, 2019, 75 (52)
[2]   Nucleophilicities and carbon basicities of DBU and DBN [J].
Baidya, M. ;
Mayr, Herbert .
CHEMICAL COMMUNICATIONS, 2008, (15) :1792-1794
[3]   Bimetallic Aluminum(salen) Catalyzed Synthesis of Oxazolidinones from Epoxides and Isocyanates [J].
Baronsky, Thilo ;
Beattie, Christopher ;
Harrington, Ross W. ;
Irfan, Reyhan ;
North, Michael ;
Osende, Javier G. ;
Young, Carl .
ACS CATALYSIS, 2013, 3 (04) :790-797
[4]   The first enantioselective [3+2] cycloaddition of epoxides to arylisocyanates: asymmetric synthesis of chiral oxazolidinone phosphonates [J].
Barros, Maria Teresa ;
Faisca Phillips, Ana Maria .
TETRAHEDRON-ASYMMETRY, 2010, 21 (21-22) :2746-2752
[5]   Mechanistic Investigation of the Reaction of Epoxides with Heterocumulenes Catalysed by a Bimetallic Aluminium Salen Complex [J].
Beattie, Christopher ;
North, Michael .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (26) :8182-8188
[6]   Polymer supported oxazolidin-2-ones derived from L-serine - a cautionary tale [J].
Bew, SP ;
Bull, SD ;
Davies, SG .
TETRAHEDRON LETTERS, 2000, 41 (39) :7577-7581
[7]   Opportunities for organocatalysis in polymer synthesis via step-growth methods [J].
Bossion, Amaury ;
Heifferon, Katherine V. ;
Meabe, Leire ;
Zivic, Nicolas ;
Taton, Daniel ;
Hedrick, James L. ;
Long, Timothy E. ;
Sardon, Haritz .
PROGRESS IN POLYMER SCIENCE, 2019, 90 :164-210
[8]   Bifunctional phase-transfer catalysts for synthesis of 2-oxazolidinones from isocyanates and epoxides [J].
Cui, Dong-Xiao ;
Li, Yue-Dan ;
Huang, Ping ;
Tian, Zhuang ;
Jia, Yan-Yan ;
Wang, Ping-An .
RSC ADVANCES, 2020, 10 (21) :12360-12364
[9]   Novel polyurethane coating technology through glycidyl carbamate chemistry [J].
Edwards, PA ;
Striemer, G ;
Webster, DC .
JCT RESEARCH, 2005, 2 (07) :517-527
[10]   Synthesis, characterization and self-crosslinking of glycidyl carbamate functional resins [J].
Edwards, Peter A. ;
Striemer, Grant ;
Webster, Dean C. .
PROGRESS IN ORGANIC COATINGS, 2006, 57 (02) :128-139
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