Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1H-azepines

被引:11
作者
Craig, Donald [1 ]
Spreadbury, Samuel R. J. [1 ]
White, Andrew J. P. [2 ]
机构
[1] Imperial Coll London, Dept Chem, Mol Sci Res Hub, White City Campus,Wood Lane, London W12 0BZ, England
[2] Imperial Coll London, Chem Crystallog Lab, Mol Sci Res Hub, White City Campus,Wood Lane, London W12 0BZ, England
基金
英国工程与自然科学研究理事会;
关键词
GLYCOSIDASE INHIBITORS; RING-EXPANSION; 1,4-BIS(ARYLSULFONYL)-1,2,3,4-TETRAHYDROPYRIDINES; ACCESS; TRANSFORMATIONS; CYCLOADDITION; IMINOSUGARS; AZEPANES; ADDUCT;
D O I
10.1039/d0cc04413j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K(2)CO(3)gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.
引用
收藏
页码:9803 / 9806
页数:4
相关论文
共 40 条
[31]   Metal-free aza-Claisen type ring expansion of vinyl aziridines: an expeditious synthesis of seven membered N-heterocycles [J].
Singh, Deepak ;
Ha, Hyun-Joon .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (12) :3093-3097
[32]  
SOETENS HP, 1980, RECL TRAV CHIM PAY B, V99, P271
[33]   Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes [J].
Thankachan, Amrutha P. ;
Sindhu, K. S. ;
Krishnan, K. Keerthi ;
Anilkumar, Gopinathan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (33) :8780-8802
[34]   Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals [J].
Vitaku, Edon ;
Smith, David T. ;
Njardarson, Jon T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (24) :10257-10274
[35]   Modular Access to Azepines by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes [J].
Wang, Gang-Wei ;
Bower, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2743-2747
[36]   AMINO-SUGAR GLYCOSIDASE INHIBITORS - VERSATILE TOOLS FOR GLYCOBIOLOGISTS [J].
WINCHESTER, B ;
FLEET, GWJ .
GLYCOBIOLOGY, 1992, 2 (03) :199-210
[37]   Pharmaceutical significance of azepane based motifs for drug discovery: A critical review [J].
Zha, Gao-Feng ;
Rakesh, K. P. ;
Manukumar, H. M. ;
Shantharam, C. S. ;
Long, Sihui .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 162 :465-494
[38]   N-Bromosuccinimide-Induced Aminocyclization-Aziridine Ring-Expansion Cascade: An Asymmetric and Highly Stereoselective Approach toward the Synthesis of Azepane [J].
Zhou, Jing ;
Yeung, Ying-Yeung .
ORGANIC LETTERS, 2014, 16 (08) :2134-2137
[39]   Rhodium( I)-Catalyzed Intermolecular Aza-[4+3] Cycloaddition of Vinyl Aziridines and Dienes: Atom-Economical Synthesis of Enantiomerically Enriched Functionalized Azepines [J].
Zhu, Chao-Ze ;
Feng, Jian-Jun ;
Zhang, Junliang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (05) :1351-1355
[40]   Synthesis of 2,3-Dihydro-1H-azepine and 1H-Azepin-2(3H)-one Derivatives From Intramolecular Condensation between Stable Tertiary Enamides and Aldehydes [J].
Zhu, Wenju ;
Zhao, Liang ;
Wang, Mei-Xiang .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12047-12057