Intramolecular Didehydro-Diels-Alder Reaction for the Synthesis of Benzo-and Dihydrobenzo-Fused Heterocycles

被引:18
作者
Bober, Ashley E. [1 ]
Proto, Justin T. [1 ]
Brummond, Kay M. [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
基金
美国国家科学基金会;
关键词
PALLADIUM-CATALYZED ADDITION; CLAISEN REARRANGEMENT; ARYLBORONIC ACID; PHARMACEUTICALS; INDOLES; ROUTE;
D O I
10.1021/acs.orglett.7b00155
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using an intramolecular didehydro-Diels-Alder reaction, ene-yne substituted pyrroles, thiophenes, and furans afford functionalized indoles, benzothiophenes, and benzofurans and the corresponding dihydroaromatic products. Product selectivity for the aromatic or dihydroaromatic product is controlled by the reaction conditions, which vary depending upon the substrate.
引用
收藏
页码:1500 / 1503
页数:4
相关论文
共 31 条
[1]   Second-Generation Process Research Towards Eletriptan: A Fischer Indole Approach [J].
Ashcroft, Christopher P. ;
Hellier, Paul ;
Pettman, Alan ;
Watkinson, Simon .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (01) :98-103
[2]   An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Ley, Steven V. ;
Nikbin, Nikzad .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :442-495
[3]   Hypoxylon pulicicidum sp nov (Ascomycota, Xylariales), a Pantropical Insecticide-Producing Endophyte [J].
Bills, Gerald F. ;
Gonzalez-Menendez, Victor ;
Martin, Jesus ;
Platas, Gonzalo ;
Fournier, Jacques ;
Persoh, Derek ;
Stadler, Marc .
PLOS ONE, 2012, 7 (10)
[4]   Intramolecular Didehydro-Diels-Alder Reaction and Its Impact on the Structure-Function Properties of Environmentally Sensitive Fluorophores [J].
Brummond, Kay M. ;
Kocsis, Laura S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (08) :2320-2329
[5]   A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans [J].
Chuang, Kangway V. ;
Kieffer, Madeleine E. ;
Reisman, Sarah E. .
ORGANIC LETTERS, 2016, 18 (18) :4750-4753
[6]   THE COMPLETE DNA-SEQUENCE OF VARICELLA-ZOSTER VIRUS [J].
DAVISON, AJ ;
SCOTT, JE .
JOURNAL OF GENERAL VIROLOGY, 1986, 67 :1759-1816
[7]   New fibrinolytic agents: Benzothiophene derivatives as inhibitors of the t-PA-PAI-1 complex formation [J].
De Nanteuil, G ;
Lila-Ambroise, C ;
Rupin, A ;
Vallez, MO ;
Verbeuren, TJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (10) :1705-1708
[8]   STEREOSELECTIVE ROUTES TO SOME UNSATURATED ALPHA-C-GLYCOPYRANOSIDES AND BETA-C-GLYCOPYRANOSIDES [J].
FRASERREID, B ;
DAWE, RD ;
TULSHIAN, DB .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (13) :1746-1749
[9]   A novel one-pot synthesis of carbazole-1,4-quinones through Pd-catalyzed cyclocarbonylation, desilylation and oxidation processes from 3-iodo-2-propenylindoles [J].
Fujii, Mami ;
Nishiyama, Takashi ;
Choshi, Tominari ;
Satsuki, Nanase ;
Fujiwaki, Takaya ;
Abe, Takumi ;
Ishikura, Minoru ;
Hibino, Satoshi .
TETRAHEDRON, 2014, 70 (09) :1805-1810
[10]   Convenient synthesis of α,α-(bisallyl and bispropargyl)-substituted amines via aza-Barbier-type reaction [J].
Guo, Tao ;
Liu, Ying-Chao ;
Li, Bo ;
Liu, Hong-Min .
TETRAHEDRON LETTERS, 2015, 56 (19) :2469-2471