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Proton‐Promoted Hydroamination of 3‐Dialkylthiomethylene‐1,4‐pentadiynes with o ‐Phenylenediamines: A Facile Route to Benzo[ b ][1,4]diazepines
Author(s) -
Zhao YuLong,
Li DaZhi,
Han XiaoDan,
Chen Li,
Liu Qun
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700547
Subject(s) - hydroamination , chemistry , alkyne , intermolecular force , proton , medicinal chemistry , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , molecule , physics , quantum mechanics
The first proton‐promoted intermolecular hydroamination reaction of the enynes, α,α‐dialkynylketene S,S ‐acetals 2 , is described. A series of benzo[ b ][1,4]diazepines, with the structures of 3 and 5 , were prepared chemo‐ and regioselectively in good to high yields by reacting the readily available 1,4‐diynes 2 with both terminal and internal alkyne functions with o ‐phenylenediamines under very mild conditions.