Domino Synthetic Strategy for Tetrahydrothiopyran Derivatives from Benzaldehydes, 2-Acetylfuran/2-Acetylthiophene, and Sodium Sulfide

被引：8
作者：
Chen, Dongdong [1 ]
Du, Weixia [1 ]
Yang, Xufeng [1 ]
Liu, Tao [1 ]
机构：
[1] Lvliang Univ, Dept Chem & Chem Engn, Lishi 033001, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 14期
关键词：
STEREOSELECTIVE-SYNTHESIS; ELEMENTAL SULFUR; ANALOGS; POTENT; REARRANGEMENT; INHIBITORS; CATALYST; BINDING; DESIGN;
D O I：
10.1021/acs.joc.0c01006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel domino reaction from benzaldehydes and 2-acetylfuran/2-acetylthiophene with sodium sulfide was developed to synthesize a series of tetrahydrothiopyran (THTP) derivatives. The reaction proceeded well to construct a tetrahydrothiopyran ring and five new bonds in one step. A mechanism is proposed, involving a stepwise Aldol/double Michael addition/Aldol (AMMA) reaction cascade. In this transformation, sodium sulfide acts as a nucleophile and base. This method is characterized by transition-metal-free, commercially available starting materials and mild reaction conditions.
引用
收藏
页码：9088 / 9095
页数：8
相关论文
共 48 条
[1]   Design, synthesis and identification of novel substituted isothiochromene analogs as potential antiviral and cytotoxic agents [J].
Abu-Hashem, Ameen A. ;
Gouda, Moustafa A. ;
Badria, Farid A. .
MEDICINAL CHEMISTRY RESEARCH, 2018, 27 (10) :2297-2311
[2]  
[Anonymous], 2006752 CCDC
[3]   A new ratiometric, colorimetric and ''turn-on'' fluorescent chemosensor for the detection of cyanide ions based on a phenol-bisthiazolopyridine hybrid [J].
Assadollahnejad, Nazafarin ;
Kargar, Maryam ;
Darabi, Hossein Reza ;
Abouali, Negar ;
Jamshidi, Shadi ;
Sharifi, Ali ;
Aghapoor, Kioumars ;
Sayahi, Hani .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (33) :13001-13009
[4]   Structure-Based Optimization of Naphthyridones into Potent ATAD2 Bromodomain Inhibitors [J].
Bamborough, Paul ;
Chung, Chun-wa ;
Furze, Rebecca C. ;
Grandi, Paola ;
Michon, Anne-Marie ;
Sheppard, Robert J. ;
Barnett, Heather ;
Diallo, Hawa ;
Dixon, David P. ;
Douault, Clement ;
Jones, Emma J. ;
Karamshi, Bhumika ;
Mitchell, Darren J. ;
Prinjha, Rab K. ;
Rau, Christina ;
Watson, Robert J. ;
Wemer, Thilo ;
Demont, Emmanuel H. .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (15) :6151-6178
[5]   A practical, efficient synthesis of 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carbaldehyde [J].
Bio, Matthew M. ;
Hansen, Karl B. ;
Gipson, John .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (05) :892-895
[6]   Camphoric acid derived sulfur containing bicyclic carboxylic acids as chiral auxiliaries in N-acyliminium ion chemistry [J].
Braeckow, J. ;
Pabel, J. ;
Mayer, R. ;
Polborn, K. ;
Wanner, K. T. .
TETRAHEDRON, 2010, 66 (36) :7279-7287
[7]   Desymmetrization by Asymmetric Copper-Catalyzed Intramolecular C-H Insertion Reactions of α-Diazo-β-oxosulfones [J].
Brouder, Thomas A. ;
Slattery, Catherine N. ;
Ford, Alan ;
Khandavilli, U. B. Rao ;
Skorepova, Eliska ;
Eccles, Kevin S. ;
Lusi, Matteo ;
Lawrence, Simon E. ;
Maguire, Anita R. .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :7543-7563
[8]   The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase [J].
Brown, MJ ;
Carter, PS ;
Fenwick, AE ;
Fosberry, AP ;
Hamprecht, DW ;
Hibbs, MJ ;
Jarvest, RL ;
Mensah, L ;
Milner, PH ;
O'Hanlon, PJ ;
Pope, AJ ;
Richardson, CM ;
West, A ;
Witty, DR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (21) :3171-3174
[9]   Diastereoselective intramolecular hetero Diels-Alder approach towards polycyclic heterocycles [J].
Ceulemans, E ;
Voets, M ;
Emmers, S ;
Uytterhoeven, K ;
Van Meervelt, L ;
Dehaen, W .
TETRAHEDRON, 2002, 58 (03) :531-544
[10]   Copper-Catalyzed and Air-Mediated Mild Cross-Dehydrogenative Coupling of Aryl Thioureas and Dialkyl H-Phosphonates: The Synthesis of Thiophosphonates [J].
Chang, Cai-Zhu ;
Liu, Xing ;
Zhu, Hui ;
Wu, Li ;
Dong, Zhi-Bing .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13530-13535
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