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. (C) 2016 Published by
Elsevier Ltd.
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. (C) 2016 Published by
Elsevier Ltd.
M3 - Article
AN - SCOPUS:84977104529
SN - 0040-4020
SP - 4867
EP - 4877
JO - Tetrahedron
JF - Tetrahedron
ER -