Aqueous MCRs of quaternary ammoniums, N-substituted formamides and sodium disulfide towards aryl thioamides

作者: Zhou Zhou , Jin-Tao Yu , Yongnan Zhou , Yan Jiang , Jiang Cheng

DOI: 10.1039/C6QO00670A

关键词: SodiumArylAmmoniumChemistryFormamidesDisulfide bondOrganic chemistryAqueous solution

摘要: A three-component reaction of quaternary ammonium salts, N-substituted formamides and aqueous sodium disulfide was developed, leading to aryl/heteroaryl thioamides in moderate good yields with functional group compatibility. This procedure featured the combination three partners, rendering an important complementary previously reported methods for synthesis aryl thioamides, beneficial chemistry transformations. No external oxidant required this procedure.

参考文章(48)
R. Bach, S. Harthong, J. Lacour, 3.20 Nitrogen- and Sulfur-Based Stevens and Related Rearrangements Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis II (Second Edition). pp. 992- 1037 ,(2014) , 10.1016/B978-0-08-097742-3.00326-8
N. Kumagai, 4.14 Reactions using Thioamide and Allylic Cyanide Comprehensive Chirality. pp. 293- 302 ,(2012) , 10.1016/B978-0-08-095167-6.00413-4
Chun-Hua Yang, Guo-Jing Li, Chao-Jun Gong, Yue-Ming Li, N,N-Dialkylaniline-Assisted Thionation of Carboxylic Amides and Esters. Tetrahedron. ,vol. 71, pp. 637- 642 ,(2015) , 10.1016/J.TET.2014.12.030
Ken Okamoto, Junpei Kuwabara, Takaki Kanbara, Secondary Thioamides as Multidentate Ligands for Functional Metal Complexes Chemistry Letters. ,vol. 44, pp. 102- 110 ,(2015) , 10.1246/CL.140996
Steven J. Coats, Jeffrey S. Link, Dennis J. Hlasta, Alternative Solvents for Elevated-Temperature Solid-Phase Parallel Synthesis. Application to Thionation of Amides Organic Letters. ,vol. 5, pp. 721- 724 ,(2003) , 10.1021/OL027493S
Takao Yamazaki, Hiroki Takahata, Synthesis of Heterocycles Using Thioamide Groups Heterocycles. ,vol. 27, pp. 1953- 1973 ,(1988) , 10.3987/REV-88-387
U. M. Dzhemilev, N. Z. Baibulatova, R. V. Kunakova, T. K. Tkachenko, G. A. Tolstikov, New approach to the synthesis of alkylthioamides using catalysts containing cobalt complexes Russian Chemical Bulletin. ,vol. 38, pp. 1202- 1206 ,(1989) , 10.1007/BF00957154
Michal Szostak, Jeffrey Aubé, Synthesis and rearrangement of a bridged thioamide Chemical Communications. pp. 7122- 7124 ,(2009) , 10.1039/B917508C