TY - JOUR
T1 - Domino reactions of cyclic enaminones leading to selective synthesis of pentacyclic indoles and its functionalization
AU - Fan, Wei
AU - Li, Yan Rong
AU - Li, Qun
AU - Jiang, Bo
AU - Li, Guigen
N1 - Funding Information:
We are grateful for financial support from the National Natural Science Foundation of China (No. 21332005 ), PAPD of Jiangsu Higher Education Institutions , Robert A. Welch Foundation ( D-1361 , USA) and National Institutes of Health ( R33DA031860 , USA), the Outstanding Youth Fund of Jiangsu Normal University ( YQ2015003 ), National Science Foundation of Jiangsu Province ( BK20151163 ), and the Open Foundation of Jiangsu Key Laboratory ( K201505 ).
Publisher Copyright:
© 2016
PY - 2016
Y1 - 2016
N2 - A new multicomponent domino reaction of cyclic enaminones with acenaphthylene-1,2-dione in an anhydride solvent has been established, providing selective protocol to pentacyclic indoles with different substituted patterns (up to 50 examples). Both substitutions on the cyclic enaminone ring and reaction temperatures showed obvious impact on the reaction pathways. For instance, selective allylic hydroxylation and allylic esterification of in situ generated indoles depend on reaction temperatures. With special substituents, the reactions underwent dehydrogenation process to give access to different substituted fused indoles with good to excellent yields. These reactions feature mild conditions, convenient one-pot operation and short reaction times. The purification of products only needs to be washed by 95% ethanol without traditional chromatography and recrystallization, which characterizes group-assisted purification (GAP) chemistry.
AB - A new multicomponent domino reaction of cyclic enaminones with acenaphthylene-1,2-dione in an anhydride solvent has been established, providing selective protocol to pentacyclic indoles with different substituted patterns (up to 50 examples). Both substitutions on the cyclic enaminone ring and reaction temperatures showed obvious impact on the reaction pathways. For instance, selective allylic hydroxylation and allylic esterification of in situ generated indoles depend on reaction temperatures. With special substituents, the reactions underwent dehydrogenation process to give access to different substituted fused indoles with good to excellent yields. These reactions feature mild conditions, convenient one-pot operation and short reaction times. The purification of products only needs to be washed by 95% ethanol without traditional chromatography and recrystallization, which characterizes group-assisted purification (GAP) chemistry.
KW - Allylic hydroxylation
KW - Esterification
KW - Fused indoles
KW - Group-assisted purification (GAP) chemistry
KW - Multicomponent domino reactions (MDRs)
UR - http://www.scopus.com/inward/record.url?scp=84977104529&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2016.06.058
DO - 10.1016/j.tet.2016.06.058
M3 - Article
AN - SCOPUS:84977104529
VL - 72
SP - 4867
EP - 4877
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 32
ER -