Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates

被引:1
作者
Ding Rou [1 ]
Shi Siyu [1 ]
Ma Chao [1 ]
Wei Wei [1 ,2 ]
Lu Yufen [1 ]
机构
[1] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Shandong, Peoples R China
[2] Chinese Acad Sci, Northwest Inst Plateau Biol, CAS Key Lab Tibetan Med Res, Xining 810008, Peoples R China
关键词
metal-free; alpha-acetalamide; glyoxylic acid; aryl isothiocyanate; TRANSAMIDATION; AMIDATION; CHEMISTRY; OXIDATION; PROGRESS; PEPTIDE; REAGENT; AMINES; CARBON;
D O I
10.6023/cjoc202403029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Metal-free condensation reaction of glyoxylic acid acetalde with aryl isothiocyanates leading to alpha-acetal amides has been reported. The present protocol, which simply utilizes 1,8-diazabicyclo(5.4.0)-undec-7-ene (DBU) as base, provides a green and efficient approach to construct a series of alpha-acetal amides in the absence of metal catalysts and stoichiometric amounts of coupling reagents.
引用
收藏
页码:2216 / 2222
页数:7
相关论文
共 45 条
[1]   Reaction of benzaldehyde with various aliphatic glycols in the presence of hydrophobic Al-MCM-41: A convenient synthesis of cyclic acetals [J].
Ajaikumar, S. ;
Pandurangan, A. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 290 (1-2) :35-43
[2]   Biosynthesis of insect spiroacetals [J].
Booth, Yvonne K. ;
Kitching, William ;
De Voss, James J. .
NATURAL PRODUCT REPORTS, 2009, 26 (04) :490-525
[3]   Chemistry of bis-spiroacetal systems: Natural products, synthesis and stereochemistry [J].
Brimble, MA ;
Furkert, DP .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (14) :1461-1484
[4]   Formyloxyacetoxyphenylmethane as an N-Formylating Reagent for Amines, Amino Acids, and Peptides [J].
Chapman, Robert S. L. ;
Lawrence, Ruth ;
Williams, Jonathan M. J. ;
Bull, Steven D. .
ORGANIC LETTERS, 2017, 19 (18) :4908-4911
[5]   NH4I-promoted N-acylation of amines via the transamidation of DMF and DMA under metal-free conditions [J].
Chen, Jiahui ;
Jia, Jing ;
Guo, Ziyi ;
Zhang, Jitan ;
Xie, Meihua .
TETRAHEDRON LETTERS, 2019, 60 (21) :1426-1429
[6]   A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines [J].
Chen, Wenteng ;
Shao, Jiaan ;
Hu, Miao ;
Yu, Wanwan ;
Giulianotti, Marc A. ;
Houghten, Richard A. ;
Yu, Yongping .
CHEMICAL SCIENCE, 2013, 4 (03) :970-976
[7]   Preparation of allylic fatty acid amides in high yield by condensation of fatty acids with allylisothiocyanate [J].
Delaveau, V ;
Mouloungui, Z ;
Gaset, A .
SYNTHETIC COMMUNICATIONS, 1996, 26 (12) :2341-2348
[8]   Enzymatic amidation for industrial applications [J].
Dorr, Brent M. ;
Fuerst, Douglas E. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2018, 43 :127-133
[9]   Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products [J].
Favre, Sylvain ;
Vogel, Pierre ;
Gerber-Lemaire, Sandrine .
MOLECULES, 2008, 13 (10) :2570-2600
[10]   Spiroacetals in insects [J].
Francke, W ;
Kitching, W .
CURRENT ORGANIC CHEMISTRY, 2001, 5 (02) :233-251