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Cyclopropenes for the Synthesis of Cyclopropane‐Fused Dihydroquinolines and Benzazepines
Author(s) -
Luo HuiXin,
Niu YouHong,
Cao XiaoPing,
Ye XinShan
Publication year - 2015
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.201500203
Subject(s) - chemistry , cyclopropane , regioselectivity , benzazepines , isomerization , ring (chemistry) , benzazepine , combinatorial chemistry , organic chemistry , catalysis
An efficient method for the construction of cyclopropane‐fused dihydroquinolines was established by a novel Povarov‐type three‐component reaction of aromatic aldehydes, anilines and cyclopropenes in the presence of trifluoromethanesulfonic acid. The reaction proceeded in a regioselective and diastereoselective manner. Furthermore, the dihydroquinolines were smoothly converted to benzazepine derivatives via a ring opening/isomerization sequence, further expanding the synthetic scope.