TY - JOUR
T1 - Synthesis of Polycyclic Benzo[b]indolo[3,2,1-de]acridines via Sequential Allenylation, Diels-Alder Cyclization, and Hydrogen Migration Reaction
AU - Zhao, Yulei
AU - Yuan, Yang
AU - Wang, Xiaoyu
AU - Li, Yanzhong
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/10/20
Y1 - 2017/10/20
N2 - A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs2CO3) was indispensable for the hydrogen migration.
AB - A novel methodology for stereoselective synthesis of benzo[b]indolo[3,2,1-de]acridines through the tandem reaction of propargylic compounds with organoboron is described, and only one diastereoisomer was obtained. The sequential procedure was triggered by Pd(0)-catalyzed allenylation of propargyl carbonate. Then, Diels-Alder cyclization and hydrogen migration processes proceeded successively to furnish the polycyclic target molecules. Control reactions suggested the base (Cs2CO3) was indispensable for the hydrogen migration.
UR - https://www.scopus.com/pages/publications/85031919629
U2 - 10.1021/acs.joc.7b01614
DO - 10.1021/acs.joc.7b01614
M3 - 文章
AN - SCOPUS:85031919629
SN - 0022-3263
VL - 82
SP - 11198
EP - 11205
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 20
ER -