期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 5, 页码 965-971出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201408
关键词
Synthetic methods; Cyclization; Fused-ring systems; Nitrogen heterocycles; Isocyanates
资金
- National Research Foundation (NRF) of Korea
- Korean government (MEST) through the SRC/ERC [R-11-2007-107-02001-0]
- WCU programs [R32-2008-000-10098-0]
- National Research Foundation of Korea [2007-0056817] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
Mild reaction conditions for the regioselective synthesis of isoquinolin-1-ones and related fused-ring heterocycles from N-Boc-protected (beta-arylethyl) carbamates are described. The reactions involved the use of Tf2O and 2-chloropyridine and isocyanates are likely to be key intermediates. The method was extended to substrates bearing less nucleophilic aryl moieties by using Lewis acid additives, such as BF3 center dot Et2O, to enhance the Friedel-Crafts-type cyclization of the isocyanate intermediates. This method allowed the synthesis of various substituted isoquinolin-1-ones, beta-carbolines, thiophene-fused ring systems and tetrahydrobenzoazepin-1-ones in good yields and with high regioselectivities.
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