Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with pyrrole and indole rings: facile synthesis of N-bridgehead azepine skeletons.
A convenient and efficient synthetic method has been developed to construct highly functionalized N-bridgehead azepine skeletons, which are of great importance in biological and pharmaceutical industry. The reaction proceeds through a rhodium(II) azavinyl carbene intermediate, which initiated the intramolecular C-H functionalization with pyrrolyl and indolyl rings. A variety of azepine derivatives were obtained in moderate to good yields under mild reaction conditions with high chemoselectivity. Several interesting derivatizations of the resulting products demonstrate that this method is synthetically valuable and useful.
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China).
Jin-Ming
JM
Yang
Cheng-Zhi
CZ
Zhu
Xiang-Ying
XY
Tang
Min
M
Shi
D001381:Azepines / Q000737:chemistry*; D002384:Catalysis; D012238:Rhodium / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D001381:Azepines; D014230:Triazoles; D012238:Rhodium
annulation; heterocycles; reaction mechanisms; rhodium; synthetic methods