Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines

被引:22
作者
Gilbert, Audrey [1 ]
Bertrand, Xavier [1 ]
Paquin, Jean-Francois [1 ]
机构
[1] Univ Laval, CGCC, PROTEO, Dept Chim, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
PENTAFLUOROSULFANYL; CHEMISTRY; SUBSTITUENTS; FLUORINE; ALCOHOLS; ANALOG; ACIDS;
D O I
10.1021/acs.orglett.8b03170
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 5-[(pentafluorosulfanyl)methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)propyl] amide to occur without elimination of the chlorine atom, a reaction pathway typically observed for beta-chloro-SF5-alkyl compounds. The products, potentially valuable SF5-containing heterocycles, are obtained in up to 97% yield.
引用
收藏
页码:7257 / 7260
页数:4
相关论文
共 38 条
[1]   New and convenient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic organic compounds [J].
Aït-Mohand, S ;
Dolbier, WR .
ORGANIC LETTERS, 2002, 4 (17) :3013-3015
[2]   Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules [J].
Altomonte, Stefano ;
Zanda, Matteo .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 143 :57-93
[3]   Structure-Activity Study of Bioisosteric Trifluoromethyl and Pentafluorosulfanyl Indole Inhibitors of the AAA ATPase p97 [J].
Alverez, Celeste ;
Arkin, Michelle R. ;
Bulfer, Stacie L. ;
Colombo, Raffaele ;
Kovaliov, Marina ;
LaPorte, Matthew G. ;
Lim, Chaemin ;
Liang, Mary ;
Moore, William J. ;
Neitz, R. Jeffrey ;
Yan, Yongzhao ;
Yue, Zhizhou ;
Huryn, Donna M. ;
Wipf, Peter .
ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (12) :1225-1230
[4]   Synthesis, antimycobacterial and cytotoxic activity of α,β-unsaturated amides and 2,4-disubstituted oxazoline derivatives [J].
Avalos-Alanis, Francisco G. ;
Hernandez-Fernandez, Eugenio ;
Carranza-Rosales, Pilar ;
Lopez-Cortina, Susana ;
Hernandez-Fernandez, Jorge ;
Ordonez, Mario ;
Guzman-Delgado, Nancy E. ;
Morales-Vargas, Alejandro ;
Velazquez-Moreno, Victor M. ;
Santiago-Mauricio, Maria G. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (04) :821-825
[5]   Organic fluorine compounds: a great opportunity for enhanced materials properties [J].
Berger, Ricarda ;
Resnati, Giuseppe ;
Metrangolo, Pierangelo ;
Weber, Edwin ;
Hulliger, Juerg .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3496-3508
[6]   A new method for the synthesis of aromatic sulfurpentafluorides and studies of the stability of the sulfurpentafluoride group in common synthetic transformations [J].
Bowden, RD ;
Comina, PJ ;
Greenhall, MP ;
Kariuki, BM ;
Loveday, A ;
Philp, D .
TETRAHEDRON, 2000, 56 (21) :3399-3408
[7]   Recent advancements in the synthesis of pentafluorosulfanyl (SF5)-containing heteroaromatic compounds [J].
Das, Prajwalita ;
Tokunaga, Etsuko ;
Shibata, Norio .
TETRAHEDRON LETTERS, 2017, 58 (52) :4803-4815
[8]   Synthesis of SF5CF2-Containing Enones and Instability of This Group in Specific Chemical Environments and Reaction Conditions [J].
Dudzinski, Piotr ;
Matsnev, Andrej V. ;
Thrasher, Joseph S. ;
Haufe, Guenter .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) :4454-4463
[9]   Successful fluorine-containing herbicide agrochemicals [J].
Fujiwara, Tomoya ;
O'Hagan, David .
JOURNAL OF FLUORINE CHEMISTRY, 2014, 167 :16-29
[10]   Applications of Fluorine in Medicinal Chemistry [J].
Gillis, Eric P. ;
Eastman, Kyle J. ;
Hill, Matthew D. ;
Donnelly, David J. ;
Meanwell, Nicholas A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (21) :8315-8359